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Synthesis 2009(15): 2596-2604  
DOI: 10.1055/s-0029-1217403
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Glycosylations of Tertiary Alcohols: Synthesis of Fully Protected Disaccharides with Sterically Demanding Groups Attached to the Sugar Core

Annika Holkenbrink, Jordi Bertrán Vicente, Daniel B. Werz*
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
Fax: +49(551)399476; e-Mail: dwerz@gwdg.de;
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Publikationsverlauf

Received 18 February 2009
Publikationsdatum:
22. Juni 2009 (online)

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Abstract

Modified gluco- and galactopyranosides with sterically demanding groups in the 4-position were synthesized. Glycosylation studies of these tertiary alcohols with glycosyl trichloroacet­imidates and glycosyl phosphates were performed. Despite steric hindrance the modified disaccharide moieties could be assembled in moderate yields.

Key words

carbohydrates - glycosylation - steric hindrance - glycosides

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