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Journal articles on the topic 'Acetonides - Deprotection'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 September 2023

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1

Poon, Kevin W. C., Kimberly M. Lovell, Kendra N. Dresner, and Apurba Datta. "Trimethylsilyl Trifluoromethanesulfonate (TMSOTf) Assisted Facile Deprotection ofN,O-Acetonides." Journal of Organic Chemistry 73, no. 2 (January 2008): 752–55. http://dx.doi.org/10.1021/jo7021923.

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2

Chari, M., and K. Syamasundar. "Polymer-Supported Ferric Chloride as a Heterogeneous Catalyst for Chemoselective Deprotection of Acetonides." Synthesis 2005, no. 05 (February 14, 2005): 708–10. http://dx.doi.org/10.1055/s-2005-861817.

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3

Xiong, Junlong, Shiqiang Yan, Ning Ding, Wei Zhang, and Yingxia Li. "Ultrasound-Assisted Selective Deprotection of Terminal Acetonides Catalyzed by Silica-Supported Boron Trifluoride." Journal of Carbohydrate Chemistry 32, no. 3 (March 24, 2013): 184–92. http://dx.doi.org/10.1080/07328303.2012.762980.

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4

Voigt, Brunhilde, Andrea Porzel, Günter Adam, Dieter Golsch, Waldemar Adam, Christoph Wagner, and Kurt Merzweiler. "Synthesis of 2,24-Diepicastasterone and 3,24-Diepicastasterone as Potential Brassinosteroid Metabolites of the Cockroach Periplaneta americana." Collection of Czechoslovak Chemical Communications 67, no. 1 (2002): 91–102. http://dx.doi.org/10.1135/cccc20020091.

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Investigations of the metabolic conversion of the phytohormone 24-epicastasterone (1) in the cockroach Periplaneta americana (L.) required the synthesis of 2,24-diepicastasterone (4), 3,24-diepicastasterone (7b) and 2-dehydro-3,24-diepicastasterone (9) as reference standards. 2,24-Diepicastasterone (4) was synthesized from 2α,3α-epoxy derivative 2 as well as from the 2β,3β-epoxy-22,23-diol 3 by acid-catalyzed water addition to the epoxy function leading to the desired 2β,3α-trans functionality. 3,24-Diepicastasterone (7b) was prepared by NaBH4-reduction of the 3-oxo derivative 6. Upon deprotection conditions from the ketol acetonides 6 and 8 in both cases 2-dehydro-3,24-diepicastasterone (9) was obtained. The structure of 2,24-diepicastasterone (4) was confirmed by X-ray analysis.

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5

Swamy, N. Raghavendra, and Y. Venkateswarlu. "A mild and efficient method for chemoselective deprotection of acetonides by bismuth(III) trichloride." Tetrahedron Letters 43, no. 42 (October 2002): 7549–52. http://dx.doi.org/10.1016/s0040-4039(02)01809-9.

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6

Sabitha, Gowravaram, G. S. Kiran Kumar Reddy, K. Bhaskar Reddy, N. Mallikarjuna Reddy, and J. S. Yadav. "Vanadium(III) chloride: A mild and efficient catalyst for the chemoselective deprotection of acetonides." Journal of Molecular Catalysis A: Chemical 238, no. 1-2 (September 2005): 229–32. http://dx.doi.org/10.1016/j.molcata.2005.05.028.

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7

Prabhu, Kandikere, and Mahagundappa Maddani. "Metal-Free Deprotection of Terminal Acetonides by Using tert-Butyl Hydroperoxide in Aqueous Medium." Synlett 2011, no. 06 (March 16, 2011): 821–25. http://dx.doi.org/10.1055/s-0030-1259917.

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8

Golden, Kathryn C., Brian T. Gregg, and John F. Quinn. "Mild, versatile, and chemoselective indium(III) triflate-catalyzed deprotection of acetonides under microwave heating conditions." Tetrahedron Letters 51, no. 31 (August 2010): 4010–13. http://dx.doi.org/10.1016/j.tetlet.2010.05.116.

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9

Xiong, Junlong, Shiqiang Yan, Ning Ding, Wei Zhang, and Yingxia Li. "ChemInform Abstract: Ultrasound-Assisted Selective Deprotection of Terminal Acetonides Catalyzed by Silica-Supported Boron Trifluoride." ChemInform 44, no. 44 (October 14, 2013): no. http://dx.doi.org/10.1002/chin.201344195.

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10

Malla Reddy, S., Y. Venkat Reddy, and Y. Venkateswarlu. "A mild and efficient method for the chemoselective deprotection of acetonides with lanthanum(III) nitrate hexahydrate." Tetrahedron Letters 46, no. 43 (October 2005): 7439–41. http://dx.doi.org/10.1016/j.tetlet.2005.08.081.

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11

Maddani, Mahagundappa R., and Kandikere R. Prabhu. "ChemInform Abstract: Metal-Free Deprotection of Terminal Acetonides by Using tert-Butyl Hydroperoxide in Aqueous Medium." ChemInform 42, no. 30 (June 30, 2011): no. http://dx.doi.org/10.1002/chin.201130206.

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12

Golden, Kathryn C., Brian T. Gregg, and John F. Quinn. "ChemInform Abstract: Mild, Versatile, and Chemoselective Indium(III) Triflate-Catalyzed Deprotection of Acetonides under Microwave Heating Conditions." ChemInform 41, no. 47 (October 28, 2010): no. http://dx.doi.org/10.1002/chin.201047055.

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13

Mahender, G., R. Ramu, C. Ramesh, and Biswanath Das. "A Simple and Facile Chemo- and Regioselective Deprotection of Acetonides Using Silica Supported Sodium Hydrogen Sulfate as a Heterogeneous Catalyst." Chemistry Letters 32, no. 8 (August 2003): 734–35. http://dx.doi.org/10.1246/cl.2003.734.

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14

MUKHERJEE, S., A. SENGUPTA, and S. C. ROY. "Environment friendly chemoselective deprotection of acetonides and cleavage of acetals and ketals in aqueous medium without using any catalyst or organic solvent." Journal of Chemical Sciences 125, no. 6 (November 2013): 1493–96. http://dx.doi.org/10.1007/s12039-013-0514-7.

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15

Mukherjee, S., A. Sengupta, and S. C. Roy. "ChemInform Abstract: Environment Friendly Chemoselective Deprotection of Acetonides and Cleavage of Acetals and Ketals in Aqueous Medium Without Using Any Catalyst or Organic Solvent." ChemInform 45, no. 14 (March 21, 2014): no. http://dx.doi.org/10.1002/chin.201414043.

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16

Fraňová, Paula, Štefan Marchalín, Peter Šafář, Matej Cvečko, Ján Moncol, Ivana Žídeková, Mohamed Othman, and Adam Daïch. "Smart and concise entry to chiral spiro[cyclopentane-indolizidine]-tetraol diastereomers as a new aza-spirocyclic framework." New Journal of Chemistry 45, no. 35 (2021): 15956–67. http://dx.doi.org/10.1039/d1nj02180j.

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17

Chandra Babu, K., R. Buchi Reddy, E. Naresh, K. Ram Mohan, G. Madhusudhan, and K. Mukkanti. "Enantioselective Synthesis of Antiepileptic Drug: (-)-Levetiracetam—Synthetic Applications of the Versatile New ChiralN-Sulfinimine." Journal of Chemistry 2013 (2013): 1–6. http://dx.doi.org/10.1155/2013/475032.

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We report an asymmetric synthesis of (-)-Levetiracetam (1) in six steps starting from versatile new chiralN-sulfinimine (3). The key step, stereoselective 1,2-addition of ethylmagnesium bromide (EtMgBr) to chiralN-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA, gave the corresponding sulfonamide (2) in high diastereoselectivity. Simultaneous deprotection and deacetylation followed by NaIO4cleavage and reduction gaveβ-amino alcohol (6). Subsequent reactions yielded the targeted compound levetiracetam (1).

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18

Matin, Mohammed Mahbubul, PhD ,, Postdoc ,, Mohammad Ibrahim, Tasnim Rahman Anisa, Ms ,, Md Rezaur Rahman, and PhD ,. "SYNTHESIS, CHARACTERIZATION, IN SILICO OPTIMIZATION, AND CONFORMATIONAL STUDIES OF METHYL 4-O-PIVALOYL-α-L-RHAMNOPYRANOSIDES." Malaysian Journal of Science 41, no. 1 (March 7, 2022): 91–105. http://dx.doi.org/10.22452/mjs.vol41no1.6.

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Considering promising biological activities of natural and synthetic rhamnopyranoside esters, we have synthesized several methyl 4-O-pivaloyl-α-L-rhamnopyranosides via selective 2,3-O-acetonide protection of methyl α-L-rhamnopyranoside (4) followed by C-4 pivaloylation, and deprotection. The synthesized 4-O-pivaloate 7 and its 2,3-di-O-esters 8a-e are characterized by spectroscopy and are optimized by using density functional theory (DFT). The free energy and bond angles thus calculated are used to establish the probable conformation(s). The 2,3-O-acetonide protected rhamnopyranosides 5-6 are found to be slightly distorted from the regular 1C4 conformation, and exist between the chair and twist-boat (skew) conformation while other pivaloyl esters 7-8a-e exist in regular 1C4 chair conformation.

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19

Li, John, May May Leong, Alastair Stewart, and Mark A. Rizzacasa. "Total synthesis of the endogenous inflammation resolving lipid resolvin D2 using a common lynchpin." Beilstein Journal of Organic Chemistry 9 (December 3, 2013): 2762–66. http://dx.doi.org/10.3762/bjoc.9.310.

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The total synthesis of the endogenous inflammation resolving eicosanoid resolvin D2 (1) is described. The key steps involved a Wittig reaction between aldehyde 5 and the ylide derived from phosphonium salt 6 to give enyne 17 and condensation of the same ylide with aldehyde 7 to afford enyne 11. Desilylation of 11 followed by hydrozirconation and iodination gave the vinyl iodide 4 and Sonogashira coupling between this compound and enyne 3 provided alkyne 18. Acetonide deprotection, partial reduction and ester hydrolysis then gave resolvin D2 (1).

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20

Banwell, Martin G., Mark J. Coster, Alison J. Edwards, Ochitha P. Karunaratne, Jason A. Smith, Lee L. Welling, and Anthony C. Willis. "A Total Synthesis of the Styryllactone (+)-Goniodiol from Naphthalene." Australian Journal of Chemistry 56, no. 6 (2003): 585. http://dx.doi.org/10.1071/ch02242.

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The cytotoxic natural product (+)-goniodiol (1) has been prepared in twelve steps from the enantiomerically pure cis-dihydrocatechol (2), which is readily obtained by microbial oxidation of naphthalene. Elaboration of compound (2) involves an initial oxidative cleavage to dialdehyde (7) followed by reduction to give diol (12). Conversion of compound (12) into acetal (17) required, inter alia, selective oxidation of the benzylic alcohol moiety followed by a metal-catalyzed decarbonylation of the resulting aldehyde. Allylation of compound (17) with allyltributylstannane in the presence of lithium perchlorate gave a ca. 2.7 : 1 mixture of alcohols (18) and (19), each of which was converted into the corresponding acrylate under standard conditions. Subjection of these ester derivatives to a ring-closing metathesis (RCM) reaction with Grubbs' first-generation catalyst gave the anticipated lactones (22) and (23). Acid-catalyzed removal of the acetonide protecting group within compound (22) then afforded (+)-goniodiol (1), while analogous deprotection of congener (23) afforded 6-epi-(+)-goniodiol (24).

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21

Shaikh, Nadim S., Santosh S. Bhor, Anil S. Gajare, Vishnu H. Deshpande, and Radhika D. Wakharkar. "Mild and facile procedure for clay-catalyzed acetonide protection and deprotection of N (Boc)-amino alcohols and protection of 1,2-diols." Tetrahedron Letters 45, no. 28 (July 2004): 5395–98. http://dx.doi.org/10.1016/j.tetlet.2004.05.079.

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22

"A Polymeric FeCl3 Catalyst for Deprotection of Acetonides." Synfacts 2005, no. 00 (July 20, 2005): 0080. http://dx.doi.org/10.1055/s-2005-869882.

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23

Jana, S., and S. C. Roy. "Ce(IV) Ammonium Nitrate Catalyzed Chemoselective Deprotection of Acetonides." ChemInform 38, no. 32 (August 7, 2007). http://dx.doi.org/10.1002/chin.200732049.

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24

Poon, Kevin W. C., Kimberly M. Lovell, Kendra N. Dresner, and Apurba Datta. "ChemInform Abstract: Trimethylsilyl Trifluoromethanesulfonate (TMSOTf) Assisted Facile Deprotection of N,O-Acetonides." ChemInform 39, no. 19 (May 6, 2008). http://dx.doi.org/10.1002/chin.200819053.

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25

Chari, M. Adharvana, and K. Syamasundar. "Polymer-Supported Ferric Chloride as a Heterogeneous Catalyst for Chemoselective Deprotection of Acetonides." ChemInform 36, no. 34 (August 23, 2005). http://dx.doi.org/10.1002/chin.200534252.

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26

Swamy, N. Raghavendra, and Y. Venkateswarlu. "A Mild and Efficient Method for Chemoselective Deprotection of Acetonides by Bismuth(III) Trichloride." ChemInform 34, no. 3 (January 21, 2003). http://dx.doi.org/10.1002/chin.200303177.

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27

Reddy, S. Malla, Y. Venkat Reddy, and Y. Venkateswarlu. "A Mild and Efficient Method for the Chemoselective Deprotection of Acetonides with Lanthanum(III) Nitrate Hexahydrate." ChemInform 37, no. 6 (February 7, 2006). http://dx.doi.org/10.1002/chin.200606200.

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28

Mahender, G., R. Ramu, C. Ramesh, and Biswanath Das. "A Simple and Facile Chemo- and Regioselective Deprotection of Acetonides Using Silica Supported Sodium Hydrogen Sulfate as a Heterogeneous Catalyst." ChemInform 34, no. 51 (December 23, 2003). http://dx.doi.org/10.1002/chin.200351068.

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29

Shaikh, Nadim S., Santosh S. Bhor, Anil S. Gajare, Vishnu H. Deshpande, and Radhika D. Wakharkar. "Mild and Facile Procedure for Clay-Catalyzed Acetonide Protection and Deprotection of N(Boc)-Amino Alcohols and Protection of 1,2-Diols." ChemInform 35, no. 42 (October 19, 2004). http://dx.doi.org/10.1002/chin.200442064.

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