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Journal articles on the topic 'Multistep synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 22 February 2025

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1

Shukla, Chinmay A., and Amol A. Kulkarni. "Automating multistep flow synthesis: approach and challenges in integrating chemistry, machines and logic." Beilstein Journal of Organic Chemistry 13 (May 19, 2017): 960–87. http://dx.doi.org/10.3762/bjoc.13.97.

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The implementation of automation in the multistep flow synthesis is essential for transforming laboratory-scale chemistry into a reliable industrial process. In this review, we briefly introduce the role of automation based on its application in synthesis viz. auto sampling and inline monitoring, optimization and process control. Subsequently, we have critically reviewed a few multistep flow synthesis and suggested a possible control strategy to be implemented so that it helps to reliably transfer the laboratory-scale synthesis strategy to a pilot scale at its optimum conditions. Due to the vast literature in multistep synthesis, we have classified the literature and have identified the case studies based on few criteria viz. type of reaction, heating methods, processes involving in-line separation units, telescopic synthesis, processes involving in-line quenching and process with the smallest time scale of operation. This classification will cover the broader range in the multistep synthesis literature.

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2

Huang, Jianhui, Caifeng Li, Liu Liu, and Xuegang Fu. "Norbornene in Organic Synthesis." Synthesis 50, no. 15 (June 25, 2018): 2799–823. http://dx.doi.org/10.1055/s-0037-1610143.

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The norbornene skeleton possesses an alkene functionality with a fixed conformation, and represents unique reactivity. The use of norbornene and analogues as substrates is overviewed; reactivities are discussed as well as the role of norbornenes as ligands assisting modern organic transformations.1 Introduction2 Synthesis of Substituted Norbornenes2.1 Preparation of Functionalized Norbornenes by Deprotonation and Substitution Reactions2.2 Preparation of Functionalized Norbornenes under Palladium-Catalyzed Reaction Conditions2.3 Alkylation of Norbornene2.4 Multistep Synthesis3 Synthesis of Substituted Norbornanes3.1 Three-Membered-Ring Formation3.2 Formation of Four-Membered Rings3.3 Five- and Six-Membered Ring Formation3.4 Syntheses of Difunctionalized Norbornanes4 Synthesis of Cyclopentanes4.1 Oxidation Reactions4.2 Ring-Opening Cross Metathesis (ROCM)4.3 Ring-Opening Metathesis Polymerization (ROMP)4.4 Palladium-Catalyzed Ring-Opening of Norbornene5 Norbornene-Mediated Reactions5.1 Palladium Insertion into Carbon–Halide Bonds5.2 Palladium Insertion into N–H and C–H Bonds5.3 Norbornene as Ligand in Mediated Reactions6 Conclusion

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3

Sakai, Naomi, and Stefan Matile. "Multistep organic synthesis of modular photosystems." Beilstein Journal of Organic Chemistry 8 (June 19, 2012): 897–904. http://dx.doi.org/10.3762/bjoc.8.102.

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Quite extensive synthetic achievements vanish in the online supporting information of publications on functional systems. Underappreciated, their value is recognized by experts only. As an example, we here focus in on the recent synthesis of multicomponent photosystems with antiparallel charge-transfer cascades in co-axial hole- and electron-transporting channels. The synthetic steps are described one-by-one, starting with commercial starting materials and moving on to key intermediates, such as asparagusic acid, an intriguing natural product, as well as diphosphonate “feet”, and panchromatic naphthalenediimides (NDIs), to finally reach the target molecules. These products are initiators and propagators for self-organizing surface-initiated polymerization (SOSIP), a new method introduced to secure facile access to complex architectures. Chemoorthogonal to the ring-opening disulfide exchange used for SOSIP, hydrazone exchange is then introduced to achieve stack exchange, which is a “switching” technology invented to drill giant holes into SOSIP architectures and fill them with functional π-stacks of free choice.

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4

Jordan, Annalisa M., Ashley E. Wilke, Tanifa L. Nguyen, Katelyn C. Capistrant, Katie R. Zarbock, Morgan E. Batiste Simms, Brandi R. Winsor, and James W. Wollack. "Multistep Microwave-Assisted Synthesis of Avobenzone." Journal of Chemical Education 99, no. 3 (February 18, 2022): 1435–40. http://dx.doi.org/10.1021/acs.jchemed.1c00818.

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5

Hayashi, Yujiro, and Shin Ogasawara. "Multistep Continuous-Flow Synthesis of (–)-Oseltamivir." Synthesis 49, no. 02 (November 3, 2016): 424–28. http://dx.doi.org/10.1055/s-2016-0036-1588899.

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6

Parlow, John J. "Simultaneous multistep synthesis using polymeric reagents." Tetrahedron Letters 36, no. 9 (February 1995): 1395–96. http://dx.doi.org/10.1016/0040-4039(95)00008-z.

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7

Glaser, John A. "Multistep organic synthesis using flow chemistry." Clean Technologies and Environmental Policy 15, no. 2 (March 31, 2013): 205–11. http://dx.doi.org/10.1007/s10098-013-0599-1.

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8

Herath, Ananda, and Nicholas D. P. Cosford. "Continuous-flow synthesis of highly functionalized imidazo-oxadiazoles facilitated by microfluidic extraction." Beilstein Journal of Organic Chemistry 13 (February 7, 2017): 239–46. http://dx.doi.org/10.3762/bjoc.13.26.

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A versatile continuous-flow synthesis of highly functionalized 1,2,4-oxadiazoles starting from carboxylic acids is reported. This process was applied to the multistep synthesis of imidazo[1,2-a]pyridin-2-yl-1,2,4-oxadiazoles, using a three reactor, multistep continuous-flow system without isolation of intermediates. This continuous-flow method was successfully combined with a single-step liquid–liquid microextraction unit to remove high boiling point polar solvents and impurities and provides the target compounds in high purity with excellent overall yields.

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9

Sharma, Mrityunjay K., Roopashri B. Acharya, Chinmay A. Shukla, and Amol A. Kulkarni. "Assessing the possibilities of designing a unified multistep continuous flow synthesis platform." Beilstein Journal of Organic Chemistry 14 (July 26, 2018): 1917–36. http://dx.doi.org/10.3762/bjoc.14.166.

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The multistep flow synthesis of complex molecules has gained momentum over the last few years. A wide range of reaction types and conditions have been integrated seamlessly on a single platform including in-line separation as well as monitoring. Beyond merely getting considered as ‘flow version’ of conventional ‘one-pot synthesis’, multistep flow synthesis has become the next generation tool for creating libraries of new molecules. Here we give a more ‘engineering’ look at the possibility of developing a ‘unified multistep flow synthesis platform’. A detailed analysis of various scenarios is presented considering 4 different classes of drugs already reported in the literature. The possible complexities that an automated and controlled platform needs to handle are also discussed in detail. Three different design approaches are proposed: (i) one molecule at a time, (ii) many molecules at a time and (iii) cybernetic approach. Each approach would lead to the effortless integration of different synthesis stages and also at different synthesis scales. While one may expect such a platform to operate like a ‘driverless car’ or a ‘robo chemist’ or a ‘transformer’, in reality, such an envisaged system would be much more complex than these examples.

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10

Sharma, M. K., J. Raval, Gwang-Noh Ahn, Dong-Pyo Kim, and A. A. Kulkarni. "Assessing the impact of deviations in optimized multistep flow synthesis on the scale-up." Reaction Chemistry & Engineering 5, no. 5 (2020): 838–48. http://dx.doi.org/10.1039/d0re00025f.

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11

Rossa, Thaís A., Nícolas S. Suveges, Marcus M. Sá, David Cantillo, and C. Oliver Kappe. "Continuous multistep synthesis of 2-(azidomethyl)oxazoles." Beilstein Journal of Organic Chemistry 14 (February 23, 2018): 506–14. http://dx.doi.org/10.3762/bjoc.14.36.

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An efficient three-step protocol was developed to produce 2-(azidomethyl)oxazoles from vinyl azides in a continuous-flow process. The general synthetic strategy involves a thermolysis of vinyl azides to generate azirines, which react with bromoacetyl bromide to provide 2-(bromomethyl)oxazoles. The latter compounds are versatile building blocks for nucleophilic displacement reactions as demonstrated by their subsequent treatment with NaN3 in aqueous medium to give azido oxazoles in good selectivity. Process integration enabled the synthesis of this useful moiety in short overall residence times (7 to 9 min) and in good overall yields.

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12

Lövei, Klára, István Greiner, János Éles, Áron Szigetvári, Miklós Dékány, Sándor Lévai, Zoltán Novák, and György István Túrós. "Multistep Continuous-Flow Synthesis of Condensed Benzothiazoles." Journal of Flow Chemistry 5, no. 2 (June 2015): 74–81. http://dx.doi.org/10.1556/1846.2015.00004.

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13

Feng, Yuhua, Yawen Wang, Jiating He, Xiaohui Song, Yee Yan Tay, Huey Hoon Hng, Xing Yi Ling, and Hongyu Chen. "Achieving Site-Specificity in Multistep Colloidal Synthesis." Journal of the American Chemical Society 137, no. 24 (June 12, 2015): 7624–27. http://dx.doi.org/10.1021/jacs.5b04310.

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14

Phimister, James R., Eric S. Fraga, and Jack W. Ponton. "The synthesis of multistep process plant configurations." Computers & Chemical Engineering 23, no. 3 (February 1999): 315–26. http://dx.doi.org/10.1016/s0098-1354(98)00276-2.

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15

Elder, John W., and Marie A. Paolillo. "4-Bromo-2-Nitroaniline: A Multistep Synthesis." Journal of Chemical Education 71, no. 6 (June 1994): A144. http://dx.doi.org/10.1021/ed071pa144.

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16

Ortega, Pedro, Miguel Guzmán, and Leonel Vera. "Useful Spreadsheet for Updating Multistep Organic Synthesis." Journal of Chemical Education 73, no. 8 (August 1996): 726. http://dx.doi.org/10.1021/ed073p726.

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17

Zhang, Tong, Yuan-Jun Song, Xiao-Yang Zhang, and Jing-Yuan Wu. "Synthesis of Silver Nanostructures by Multistep Methods." Sensors 14, no. 4 (March 25, 2014): 5860–89. http://dx.doi.org/10.3390/s140405860.

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18

Yang, Jye-Shane, Hsin-Hau Huang, and Shih-Hsun Lin. "Facile Multistep Synthesis of Isotruxene and Isotruxenone†." Journal of Organic Chemistry 74, no. 10 (May 15, 2009): 3974–77. http://dx.doi.org/10.1021/jo900299q.

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19

Hartman, Ryan L, John R Naber, Stephen L Buchwald, and Klavs F Jensen. "Multistep Microchemical Synthesis Enabled by Microfluidic Distillation." Angewandte Chemie International Edition 49, no. 5 (December 18, 2009): 899–903. http://dx.doi.org/10.1002/anie.200904634.

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20

Hartman, Ryan L, John R Naber, Stephen L Buchwald, and Klavs F Jensen. "Multistep Microchemical Synthesis Enabled by Microfluidic Distillation." Angewandte Chemie 122, no. 5 (January 25, 2010): 911–15. http://dx.doi.org/10.1002/ange.200904634.

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21

Zippi, Elizabeth M., John Grover, Mary Beth Valiulis, and Heather C. Cheek. "A Multistep Microscale Synthesis of Poly(styrene)." Microchemical Journal 56, no. 1 (May 1997): 138–40. http://dx.doi.org/10.1006/mchj.1997.1479.

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22

Bloemendal, Victor R. L. J., Mathilde A. C. H. Janssen, Jan C. M. van Hest, and Floris P. J. T. Rutjes. "Continuous one-flow multi-step synthesis of active pharmaceutical ingredients." Reaction Chemistry & Engineering 5, no. 7 (2020): 1186–97. http://dx.doi.org/10.1039/d0re00087f.

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23

Jürjens, Gerrit, Andreas Kirschning, and David A. Candito. "Lessons from the Synthetic Chemist Nature." Natural Product Reports 32, no. 5 (2015): 723–37. http://dx.doi.org/10.1039/c4np00160e.

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Nature's strategy of performing ideal multistep (bio)synthesis are based on multicatalysis, domino reactions, iteration and compartmentation. These are discussed and compared with chemical synthesis in this conceptual review.

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24

Ren, Yun-Lai, Jianji Wang, Xinzhe Tian, Fangping Ren, Xinqiang Cheng, and Shuang Zhao. "Direct Conversion of Benzyl Ethers into Aryl Nitriles." Synlett 29, no. 18 (October 16, 2018): 2444–48. http://dx.doi.org/10.1055/s-0037-1611062.

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A direct method was developed for the conversion of benzyl ethers into aryl nitriles by using NH4OAc as the nitrogen source and oxygen as the terminal oxidant with catalysis by TEMPO/HNO3; the method is valuable for both the synthesis of aromatic nitriles and for the deprotection of ether-protected hydroxy groups to form nitrile groups in multistep organic syntheses.

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25

Boger, Dale L., Wenying Chai, and Qing Jin. "Multistep Convergent Solution-Phase Combinatorial Synthesis and Deletion Synthesis Deconvolution." Journal of the American Chemical Society 120, no. 29 (July 1998): 7220–25. http://dx.doi.org/10.1021/ja9803557.

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26

Lourens, Anna C. U., David Gravestock, Robyn L. van Zyl, Heinrich C. Hoppe, Natasha Kolesnikova, Supannee Taweechai, Yongyuth Yuthavong, Sumalee Kamchonwongpaisan, and Amanda L. Rousseau. "Design, synthesis and biological evaluation of 6-aryl-1,6-dihydro-1,3,5-triazine-2,4-diamines as antiplasmodial antifolates." Organic & Biomolecular Chemistry 14, no. 33 (2016): 7899–911. http://dx.doi.org/10.1039/c6ob01350c.

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27

Li, Li-Jun, Ying-Xia Song, Yan-Su Gao, Yan-Feng Li, and Jian-Feng Zhang. "Solvent-free Synthesis of Nitriles from Aldehydes Catalyzed by KF/Al2O3, Montmorillonite KSF and K10." E-Journal of Chemistry 3, no. 3 (2006): 164–68. http://dx.doi.org/10.1155/2006/709594.

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Multistep and one-pot conversion of aldehydes to nitriles were carried out conveniently with out solvent using KF/Al2O3, montmorillonite KSF and K10 as catalyst, under microwave irradiation. The reactions are completed within 6-8 min to give satisfactory yields. KF/Al2O3was more effective catalyst both in multistep procedure and one-pot reaction.

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28

Harsanyi, Antal, and Graham Sandford. "Fluorine gas for life science syntheses: green metrics to assess selective direct fluorination for the synthesis of 2-fluoromalonate esters." Green Chemistry 17, no. 5 (2015): 3000–3009. http://dx.doi.org/10.1039/c5gc00402k.

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29

Darzac, Magali, Stéphanie Montésinos, André Collet, and Jean-Pierre Dutasta. "Synthesis of Complementary Hydrogen Bonding Cyclotriveratrylenes." Journal of Chemical Research 2002, no. 8 (August 2002): 359–60. http://dx.doi.org/10.3184/030823402103172482.

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Two new cyclotriveratrylenes CTV-1 and CTV-2 bearing complementary H-bond donor-acceptor substituents were prepared from 4-hydroxy-3-methoxybenzyl alcohol following a multistep strategy to introduce melamine or cyanuric acid substituents.

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30

Axelsson, A., E. Hammarvid, L. Ta, and H. Sundén. "Asymmetric aerobic oxidative NHC-catalysed synthesis of dihydropyranones utilising a system of electron transfer mediators." Chemical Communications 52, no. 77 (2016): 11571–74. http://dx.doi.org/10.1039/c6cc06060a.

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31

Pétry, Nicolas, Thibaut Vanderbeeken, Astrid Malher, Yoan Bringer, Pascal Retailleau, Xavier Bantreil, and Frédéric Lamaty. "Mechanosynthesis of sydnone-containing coordination complexes." Chemical Communications 55, no. 64 (2019): 9495–98. http://dx.doi.org/10.1039/c9cc04673a.

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32

Ireni, Nagaraj Goud, Ramanuj Narayan, Pratyay Basak, and Kothapalli Venkata Suryanarayana Raju. "Functional polyurethane–urea coatings from sulfur rich hyperbranched polymers and an evaluation of their anticorrosion and optical properties." New Journal of Chemistry 40, no. 9 (2016): 8081–92. http://dx.doi.org/10.1039/c6nj00373g.

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33

Pitínová-Štekrová, Martina, Pavla Eliášová, Tobias Weissenberger, Mariya Shamzhy, Zuzana Musilová, and Jiří Čejka. "Highly selective synthesis of campholenic aldehyde over Ti-MWW catalysts by α-pinene oxide isomerization." Catalysis Science & Technology 8, no. 18 (2018): 4690–701. http://dx.doi.org/10.1039/c8cy01231h.

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34

Howard, Joseph L., William Nicholson, Yerbol Sagatov, and Duncan L. Browne. "One-pot multistep mechanochemical synthesis of fluorinated pyrazolones." Beilstein Journal of Organic Chemistry 13 (September 14, 2017): 1950–56. http://dx.doi.org/10.3762/bjoc.13.189.

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Solventless mechanochemical synthesis represents a technique with improved sustainability metrics compared to solvent-based processes. Herein, we describe a methodical process to run one solventless reaction directly into another through multistep mechanochemistry, effectively amplifying the solvent savings. The approach has to consider the solid form of the materials and compatibility of any auxiliary used. This has culminated in the development of a two-step, one-jar protocol for heterocycle formation and subsequent fluorination that has been successfully applied across a range of substrates, resulting in 12 difluorinated pyrazolones in moderate to excellent yields.

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35

Pieber, Bartholomäus, Kerry Gilmore, and Peter H. Seeberger. "Integrated flow processing — challenges in continuous multistep synthesis." Journal of Flow Chemistry 7, no. 3–4 (September 2017): 129–36. http://dx.doi.org/10.1556/1846.2017.00016.

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36

Turkyilmaz, Murat, and Fatma Genc. "Multistep Synthesis of Phosphazene Derivative of Chenodeoxycholicacid (CDCA)." Phosphorus, Sulfur, and Silicon and the Related Elements 189, no. 11 (October 21, 2014): 1723–31. http://dx.doi.org/10.1080/10426507.2014.887080.

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37

Gartner, Zev J., Matthew W. Kanan, and David R. Liu. "Multistep Small-Molecule Synthesis Programmed by DNA Templates." Journal of the American Chemical Society 124, no. 35 (September 2002): 10304–6. http://dx.doi.org/10.1021/ja027307d.

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38

McQuade, D. Tyler, and Peter H. Seeberger. "Applying Flow Chemistry: Methods, Materials, and Multistep Synthesis." Journal of Organic Chemistry 78, no. 13 (June 20, 2013): 6384–89. http://dx.doi.org/10.1021/jo400583m.

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39

Li, Yizhou, Peng Zhao, Mingda Zhang, Xianyuan Zhao, and Xiaoyu Li. "Multistep DNA-Templated Synthesis Using a Universal Template." Journal of the American Chemical Society 135, no. 47 (November 18, 2013): 17727–30. http://dx.doi.org/10.1021/ja409936r.

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40

Hansen, Henrik C., Roger Olsson, Glenn Croston, and Carl-Magnus Andersson. "Multistep solution-Phase parallel synthesis of spiperone analogues." Bioorganic & Medicinal Chemistry Letters 10, no. 21 (November 2000): 2435–39. http://dx.doi.org/10.1016/s0960-894x(00)00483-2.

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41

Li, Lianhai, and Waepril Kimberly S. Chua. "One-pot multistep synthesis of 3-aminoindolizine derivatives." Tetrahedron Letters 52, no. 12 (March 2011): 1392–94. http://dx.doi.org/10.1016/j.tetlet.2011.01.087.

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42

PARLOW, J. J. "ChemInform Abstract: Simultaneous Multistep Synthesis Using Polymeric Reagents." ChemInform 26, no. 49 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199549110.

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43

Graham, Kate J., Chris P. Schaller, Brian J. Johnson, and John B. Klassen. "Student-Designed Multistep Synthesis Projects in Organic Chemistry." Chemical Educator 7, no. 6 (December 2002): 376–78. http://dx.doi.org/10.1007/s00897020612a.

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44

Yang, Yang, Xiao Hui Wang, and Long Tu Li. "Synthesis of TiO₂ Nanotube Arrays Through Multistep Anodization." Key Engineering Materials 368-372 (February 2008): 526–28. http://dx.doi.org/10.4028/www.scientific.net/kem.368-372.526.

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Multistep electrochemical anodization is an electrochemical experiment orderly conducting in different electrolytes. In this paper, TiO2 nanotube arrays have been firstly anodic grown in aqueous electrolyte (H3PO4/HF) and later anodic grown in organic electrolyte (glycerol/NH4F). Compared with separately anodizing in aqueous and organic electrolyte, the morphology of the resulting nanotube arrays can be optimized. SEM images showed that the obtained nanotubes have a length of more than 2 μm and single-pore diameter ranging from 120 to 150 nm. The current work indicates that the multistep electrochemical anodization has a contribution to the optimization of the morphology of TiO2 nanotube arrays.

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45

Ermert, Johannes. "18F-Labelled Intermediates for Radiosynthesis by Modular Build-Up Reactions: Newer Developments." BioMed Research International 2014 (2014): 1–15. http://dx.doi.org/10.1155/2014/812973.

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This brief review gives an overview of newer developments in18F-chemistry with the focus on small18F-labelled molecules as intermediates for modular build-up syntheses. The short half-life (<2 h) of the radionuclide requires efficient syntheses of these intermediates considering that multistep syntheses are often time consuming and characterized by a loss of yield in each reaction step. Recent examples of improved synthesis of18F-labelled intermediates show new possibilities for no-carrier-added ring-fluorinated arenes, novel intermediates for tri[18F]fluoromethylation reactions, and18F-fluorovinylation methods.

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46

Zaman, Hina, Aamer Saeed, Hammad Ismail, Sadaf Anwaar, Muhammad Latif, Muhammad Zaffar Hashmi, and Hesham R. El-Seedi. "Novel pyrimidine linked acyl thiourea derivatives as potent α-amylase and proteinase K inhibitors: design, synthesis, molecular docking and ADME studies." RSC Advances 14, no. 45 (2024): 33235–46. http://dx.doi.org/10.1039/d4ra05799f.

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47

Liang, Steven H., and Neil Vasdev. "Total Radiosynthesis: Thinking Outside ‘the Box'." Australian Journal of Chemistry 68, no. 9 (2015): 1319. http://dx.doi.org/10.1071/ch15406.

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The logic of total synthesis transformed a stagnant state of chemistry when there was a paucity of methods and reagents to synthesize pharmaceuticals. Molecular imaging by positron emission tomography (PET) is now experiencing a renaissance in the way radiopharmaceuticals are synthesized; however, a paradigm shift is desperately needed in the radiotracer discovery pipeline to accelerate drug development. As with most drugs, most radiotracers also fail, therefore expeditious evaluation of tracers in preclinical models before optimization or derivatization of the lead molecules is necessary. Furthermore the exact position of the 11C and 18F radionuclide in tracers is often critical for metabolic considerations, and flexible methodologies to introduce radionuclides are needed. A challenge in PET radiochemistry is the limited choice of labelled building blocks available with carbon-11 (11C; half-life ~20 min) and fluorine-18 (18F; half-life ~2 h). In fact, most drugs cannot be labelled with 11C or 18F owing to a lack of efficient and diverse radiosynthetic methods. Routine radiopharmaceutical production generally relies on the incorporation of the isotope at the last or penultimate step of synthesis. Such reactions are conducted within the constraints of an automated synthesis unit (‘box’), which has further stifled the exploration of multistep reactions with short-lived radionuclides. Radiopharmaceutical synthesis can be transformed by considering logic of total synthesis to develop novel approaches for 11C- and 18F-radiolabelling complex molecules via retrosynthetic analysis and multistep reactions. As a result of such exploration, new methods, reagents, and radiopharmaceuticals for in vivo imaging studies are discovered and are critical to work towards our ultimate, albeit impossible goal – a concept we term as total radiosynthesis – to radiolabel virtually any molecule. In this account, we show how multistep radiochemical reactions have impacted our radiochemistry program, with prominent examples from others, focusing on impact towards human imaging studies. As the goal of total synthesis is to be concise, we strive to simplify the syntheses of radiopharmaceuticals. New clinically useful strategies, including [11C]CO2 fixation, which has enabled library radiosynthesis, as well as radiofluorination of non-activated arenes via iodonium ylides are highlighted. We also showcase state-of-the-art automation technologies, including microfluidic flow chemistry for radiopharmaceutical production.

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48

Bell, Russell A., Kieran C. Dickson, and John F. Valliant. "The total synthesis of a technetium chelate - tamoxifen complex." Canadian Journal of Chemistry 77, no. 1 (January 1, 1999): 146–54. http://dx.doi.org/10.1139/v98-220.

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A potential agent for imaging breast cancer has been synthesized by derivatization of the anti-estrogen tamoxifen. A multistep synthesis was required to conjugate a technetium chelate to tamoxifen in such a fashion that the biodistribution of the complex should mimic that of the parent compound.Key words: tamoxifen, radioimaging, technetium, synthesis.

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49

Damha, Masad José, Nassim Usman, and Kelvin Kenneth Ogilvie. "Solution and solid phase chemical synthesis of arabinonucleotides." Canadian Journal of Chemistry 67, no. 5 (May 1, 1989): 831–39. http://dx.doi.org/10.1139/v89-129.

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A fast and convenient procedure for the chemical synthesis of arabinonucleotides, which eliminates the multistep protection of the arabinonucleoside building blocks, is described. The results of these studies were successfully applied to the automated chemical synthesis of the hexanucleotide 5′-aUpaApaUpaApaUpaA-3′. Both solution and solid phase phosphite triester procedures are described. Keywords: arabinonucleotides, arabinophosphoramidites, automated chemical synthesis, protected arabinonucleosides.

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50

Ardila-Fierro, Karen J., Andrij Pich, Marc Spehr, José G. Hernández, and Carsten Bolm. "Synthesis of acylglycerol derivatives by mechanochemistry." Beilstein Journal of Organic Chemistry 15 (March 29, 2019): 811–17. http://dx.doi.org/10.3762/bjoc.15.78.

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Abstract:

In recent times, many biologically relevant building blocks such as amino acids, peptides, saccharides, nucleotides and nucleosides, etc. have been prepared by mechanochemical synthesis. However, mechanosynthesis of lipids by ball milling techniques has remained essentially unexplored. In this work, a multistep synthetic route to access mono- and diacylglycerol derivatives by mechanochemistry has been realized, including the synthesis of diacylglycerol-coumarin conjugates.

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