Literature DB >> 12688743

Oxazolidinone protection of N-acetylglucosamine confers high reactivity on the 4-hydroxy group in glycosylation.

David Crich1, A U Vinod.   

Abstract

[reaction: see text] The preparation of a convenient oxazolidinone protected N-acetyl glucosamine 4-OH derivative is reported. This substance exhibits enhanced reactivity as a glycosyl acceptor in a variety of coupling methods, the products of which are converted to the target N-acetylglucosaminyl saccharides under very mild conditions.

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Year:  2003        PMID: 12688743     DOI: 10.1021/ol0342305

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


  9 in total

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2.  Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series.

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Journal:  Carbohydr Res       Date:  2012-06-07       Impact factor: 2.104

3.  Stereocontrolled Synthesis of the Equatorial Glycosides of 3-Deoxy-d-manno-oct-2-ulosonic Acid: Role of Side Chain Conformation.

Authors:  Philemon Ngoje; David Crich
Journal:  J Am Chem Soc       Date:  2020-04-14       Impact factor: 15.419

4.  Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

Authors:  David Crich
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

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Journal:  Carbohydr Res       Date:  2006-01-26       Impact factor: 2.104

6.  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

7.  Synthesis of 6-PEtN-α-D-GalpNAc-(1->6)-β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-β-D-Galp-(1->4)-β-D-Glcp, a Haemophilus influenzae lipopolysacharide structure, and biotin and protein conjugates thereof.

Authors:  Andreas Sundgren; Martina Lahmann; Stefan Oscarson
Journal:  Beilstein J Org Chem       Date:  2010-07-26       Impact factor: 2.883

8.  Imposing the trans/gauche conformation on a sialic acid donor with a 5-N,7-O-oxazinanone group: effect on glycosylation stereoselectivity.

Authors:  David Crich; Baolin Wu
Journal:  Tetrahedron       Date:  2008-02-25       Impact factor: 2.457

9.  The influence of acceptor nucleophilicity on the glycosylation reaction mechanism.

Authors:  S van der Vorm; T Hansen; H S Overkleeft; G A van der Marel; J D C Codée
Journal:  Chem Sci       Date:  2016-11-09       Impact factor: 9.825

  9 in total

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