Literature DB >> 11405681

A new C(1)-auxiliary for anomeric stereocontrol in the synthesis of alpha-sialyl glycosides.

J M Haberman1, D Y Gin.   

Abstract

The installation of the novel N,N-dimethylglycolamide ester auxiliary onto the C(1)-position of protected neuraminic acid donors allows for the exploitation of C(1)-neighboring group participation to generate sialoside conjugates with good to excellent alpha-selectivity under a variety of sialylation protocols, including those that would otherwise lead to nonselective or beta-selective sialoside products.

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Year:  2001        PMID: 11405681     DOI: 10.1021/ol015854i

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


  5 in total

Review 1.  Advances in the biology and chemistry of sialic acids.

Authors:  Xi Chen; Ajit Varki
Journal:  ACS Chem Biol       Date:  2010-02-19       Impact factor: 5.100

2.  Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.

Authors:  Asiri A Hettikankanamalage; Robert Lassfolk; Filip S Ekholm; Reko Leino; David Crich
Journal:  Chem Rev       Date:  2020-07-05       Impact factor: 60.622

3.  Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups.

Authors:  David Crich; Prasanna Jayalath; Thomas K Hutton
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

4.  O-sialylation with N-acetyl-5-n,4-o-carbonyl-protected thiosialoside donors in dichloromethane: facile and selective cleavage of the oxazolidinone ring.

Authors:  David Crich; Wenju Li
Journal:  J Org Chem       Date:  2007-03-06       Impact factor: 4.354

Review 5.  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

  5 in total

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