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Synthesis 2010(20): 3481-3485  
DOI: 10.1055/s-0030-1258200
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Acylation of 3,4-OH Free d-Glucosamines: A Rapid Access to Orthogonally Functionalized Building Blocks

Markus Sebastian Ehret, Mickael Virlouvet, Moritz Bosse Biskup*
Karlsruher Institut für Technologie (KIT), Institut für Organische Chemie, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)6085637; e-Mail: biskup@kit.edu;
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Publication History

Received 6 April 2010
Publication Date:
05 August 2010 (online)

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Abstract

A method for the regioselective O-acylation of 3,4-OH free d-glucosamines via stannylene acetal methodology was developed. From fully acetylated 2-N-trichloroacetyl-d-glucosamine, 4-OH free d-glucosamine derivatives bearing orthogonal protecting group patterns were prepared.

Key words

carbohydrates - protecting groups - regioselectivity - stannylene acetals - glycosylaminoglycans

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