Volume 27, Issue 11
Natural Products
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ChemInform Abstract: Stereoselective Preparation of Alkyl Glycosides of 2-Acetamido-2-deoxy- α-D-glucopyranose by Nonclassical Halide-Ion Catalysis and Synthesis and NMR Spectroscopy of α-D-Gal p-(1 → 3)-. alpha.-D-Glc pNAc-OMe.

V. POZSGAY

V. POZSGAY

Lab. Dev. Mol. Immun., NIH, Bethesda, MD 20892, USA

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B. COXON

B. COXON

Lab. Dev. Mol. Immun., NIH, Bethesda, MD 20892, USA

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First published: March 12, 1996

Abstract

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ChemInform Abstract

An efficient halide ion catalyzed stereocontrolled synthesis of simple glycosides such as (III) is reported. The methyl glycoside (IIIa) is converted into the title disaccharide (IX), which represents a part of the O-polysaccharide of the lipopolysaccharide of the human pathogen Shigella dysenteriae type 1.

chemical structure image

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