Synthesis 2006(13): 2117-2120  
DOI: 10.1055/s-2006-942407
PAPER
© Georg Thieme Verlag Stuttgart · New York

Novel Approach towards C-C-Linked Carbohydrate Dimers via Claisen Rearrangement of a Disaccharide Allyl Ketene Acetal

Stefan Jürs, Joachim Thiem*
Institut für Organische Chemie der Universität, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
Fax: +49(40)428384325; e-Mail: joachim.thiem@chemie.uni-hamburg.de;
Further Information

Publication History

Received 11 April 2006
Publication Date:
08 June 2006 (online)

Abstract

A disaccharide derivative was synthesised by coupling tri-O-benzyl-d-glucal with an allylic sugar alcohol in a glycosyl­oxy­selenation reaction. Subsequent oxidation followed by syn-elimination of the selenoxide and in situ rearrangement of the intermediate allyl ketene acetal gave novel C-C-linked saccharide dimers.