4.4 Article

The surprise synthesis of α-GlcNAc 1-C-sulfonates

Journal

TETRAHEDRON LETTERS
Volume 43, Issue 34, Pages 6075-6078

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(02)01218-2

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Oxidation of GlcNAc thiazoline in the presence of an alcohol affords no glycosidation products, but rather the alkyl alpha-GlcNAc 1-C-sulfonate. E2 cleavage of the sulfonate ester and then O-deacetylation gives the alpha-GlcNAc 1-C-sulfonic acid, a new type of carbohydrate derivative. (C) 2002 Elsevier Science Ltd. All rights reserved.

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