Oxazolidinone Protection of N-Acetylglucosamine Confers High Reactivity on the 4-Hydroxy Group in Glycosylation
- 20 March 2003
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (8) , 1297-1300
- https://doi.org/10.1021/ol0342305
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.Keywords
This publication has 24 references indexed in Scilit:
- Solid-Phase Synthesis of β-MannosidesJournal of the American Chemical Society, 2002
- Oxazolidinone Protected 2-Amino-2-deoxy-d-glucose Derivatives as Versatile Intermediates in Stereoselective Oligosaccharide Synthesis and the Formation of α-Linked GlycosidesJournal of the American Chemical Society, 2001
- Toward Fully Synthetic Homogeneous Glycoproteins: A High Mannose Core Containing Glycopeptide Carrying Full H-Type 2 Human Blood Group SpecificityAngewandte Chemie International Edition in English, 2001
- Dehydrative Glycosylation with Activated Diphenyl Sulfonium Reagents. Scope, Mode of C(1)-Hemiacetal Activation, and Detection of Reactive Glycosyl IntermediatesJournal of the American Chemical Society, 2000
- Highly Diastereoselective α-Mannopyranosylation in the Absence of Participating Protecting GroupsThe Journal of Organic Chemistry, 2000
- Generalizing Glycosylation: Synthesis of the Blood Group Antigens Lea, Leb, and Lex Using a Standard Set of Reaction ConditionsJournal of the American Chemical Society, 1996
- Chemically Synthesized Oligosaccharides, 1994. A Searchable Table of Glycosidic Linkages.Journal of Carbohydrate Chemistry, 1995
- Two New Orthogonal Amine-Protecting Groups that can be Cleaved under Mild or Neutral ConditionsJournal of the American Chemical Society, 1995
- New Methods for the Synthesis of Glycosides and Oligosaccharides—Are There Alternatives to the Koenigs‐Knorr Method? [New Synthetic Methods (56)]Angewandte Chemie International Edition in English, 1986
- Advances in Selective Chemical Syntheses of Complex OligosaccharidesAngewandte Chemie International Edition in English, 1982