Literature DB >> 31490529

Triflic acid-mediated synthesis of thioglycosides.

Samira Escopy1, Yashapal Singh1, Alexei V Demchenko1.   

Abstract

An efficient synthesis of thioglycosides from per-acetates in the presence of triflic acid is described. The developed protocol features high reaction rates and product yields. Some reactive sugar series give high efficiency in the presence of sub-stoichiometric trifluoromethanesulfonic acid (TfOH) in contrast to other known protocols that require multiple equivalents of Lewis acids to reach high conversion rates.

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Year:  2019        PMID: 31490529     DOI: 10.1039/c9ob01610d

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  6 in total

1.  Syntheses of Salmonella Paratyphi A Associated Oligosaccharide Antigens and Development towards Anti-Paratyphoid Fever Vaccines.

Authors:  Debashis Dhara; Scott M Baliban; Chang-Xin Huo; Zahra Rashidijahanabad; Khandra T Sears; Setare Tahmasebi Nick; Anup Kumar Misra; Sharon M Tennant; Xuefei Huang
Journal:  Chemistry       Date:  2020-10-22       Impact factor: 5.236

2.  HPLC-Based Automated Synthesis of Glycans in Solution.

Authors:  Samira Escopy; Yashapal Singh; Keith J Stine; Alexei V Demchenko
Journal:  Chemistry       Date:  2022-05-25       Impact factor: 5.020

3.  Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature.

Authors:  Yao Liu; Xiao-Bing Yu; Xiang-Mei Zhang; Qian Zhong; Li-Hua Liao; Nan Yan
Journal:  RSC Adv       Date:  2021-08-04       Impact factor: 4.036

4.  A Streamlined Regenerative Glycosylation Reaction: Direct, Acid-Free Activation of Thioglycosides.

Authors:  Samira Escopy; Yashapal Singh; Keith J Stine; Alexei V Demchenko
Journal:  Chemistry       Date:  2020-11-30       Impact factor: 5.236

5.  Direct, stereoselective thioglycosylation enabled by an organophotoredox radical strategy.

Authors:  Peng Ji; Yueteng Zhang; Feng Gao; Fangchao Bi; Wei Wang
Journal:  Chem Sci       Date:  2020-10-19       Impact factor: 9.825

6.  SnCl4-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives.

Authors:  Kesatebrhan Haile Asressu; Cheng-Chung Wang
Journal:  Beilstein J Org Chem       Date:  2019-12-23       Impact factor: 2.883

  6 in total

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