Issue 38, 2011
From the journal:

Chemical Communications

Reducing the conformational flexibility of carbohydrates: locking the 6-hydroxylgroup by cyclopropanes†

Christian Brand,a   Markus Granitzka,b   Dietmar Stalkeb  and  Daniel B. Werz*a  

* Corresponding authors

a Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstr. 2, D-377077 Göttingen, Germany
E-mail: dwerz@gwdg.de
Fax: +49(551)399476
Tel: +49(551)393251

b Institut für Anorganische Chemie der Georg-August-Universität Göttingen, Tammannstr. 4, D-377077 Göttingen, Germany

Abstract

The 6-hydroxyl group of hexopyranosides was stereochemically locked by the spiroannelation of a cyclopropane unit at C-5. The corresponding glucose and mannose derivatives were prepared and their behaviour in glycosidation reactions was studied.

Graphical abstract: Reducing the conformational flexibility of carbohydrates: locking the 6-hydroxyl group by cyclopropanes

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Article information

DOI
https://doi.org/10.1039/C1CC14025F
Article type
Communication
Submitted
05 Jul 2011
Accepted
09 Aug 2011
First published
05 Sep 2011

Chem. Commun., 2011,47, 10782-10784

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Reducing the conformational flexibility of carbohydrates: locking the 6-hydroxyl group by cyclopropanes

C. Brand, M. Granitzka, D. Stalke and D. B. Werz, Chem. Commun., 2011, 47, 10782 DOI: 10.1039/C1CC14025F

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