Literature DB >> 10990435

A convenient preparation of glycosyl chlorides from aryl/alkyl thioglycosides.

S Sugiyama1, J M Diakur.   

Abstract

[reaction: see text]Because of the vast structural diversity encountered in the field of glycobiology, versatile methods for orthogonal oligosaccharide assembly are always of interest. Reported herein is the preparation of glycosyl chloride donors obtained by reaction of the corresponding thioglycoside precursors with chlorosulfonium chloride reagent 4. The crude chlorides thus obtained can be used directly in subsequent glycosylation reactions, and examples of the generality of this approach are provided.

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Year:  2000        PMID： 10990435     DOI： 10.1021/ol0063050

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  4 in total

1.  Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.

Authors:  Yongho Park; Kaid C Harper; Nadine Kuhl; Eugene E Kwan; Richard Y Liu; Eric N Jacobsen
Journal:  Science       Date:  2017-01-13       Impact factor: 47.728

2.  Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions.

Authors:  Peng Wen; Christopher J Simmons; Zhi-Xiong Ma; Stephanie A Blaszczyk; Paul G Balzer; Wenjing Ye; Xiyan Duan; Hao-Yuan Wang; Dan Yin; Christopher M Stevens; Weiping Tang
Journal:  Org Lett       Date:  2020-02-06       Impact factor: 6.005

Review 3.  Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

Authors:  Yashapal Singh; Scott A Geringer; Alexei V Demchenko
Journal:  Chem Rev       Date:  2022-06-08       Impact factor: 72.087

4.  An armed-disarmed approach for blocking aglycon transfer of thioglycosides.

Authors:  Zhitao Li; Jeffrey C Gildersleeve
Journal:  Tetrahedron Lett       Date:  2007-01-22       Impact factor: 2.415
  4 in total

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