Issue 21, 2012
From the journal:

Chemical Communications

β-Rhamnosides from 6-thio mannosides†

Alphert E. Christina,a   Daan van der Es,a   Jasper Dinkelaar,a   Hermen S. Overkleeft,a   Gijsbert A. van der Marel*a  and  Jeroen D. C. Codée*a  

* Corresponding authors

a Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands
E-mail: marel_g@chem.leidenuniv.nl, jcodee@chem.leidenuniv.nl
Tel: +31 715274280X

Abstract

Upon condensation of 6-thio-6-deoxy-mannosyl donors 1,2-cis products are obtained with a high degree of stereoselectivity. Subsequent reductive removal of the 6-thio functionality gives 1,2-cisrhamnosides. The 1,2-cis-selectivity can be rationalized with a product forming 3H4-oxocarbenium, which is in equilibrium with a bridged sulfonium intermediate.

Graphical abstract: β-Rhamnosides from 6-thio mannosides

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Article information

DOI
https://doi.org/10.1039/C2CC17623H
Article type
Communication
Submitted
06 Dec 2011
Accepted
17 Jan 2012
First published
18 Jan 2012

Chem. Commun., 2012,48, 2686-2688

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β-Rhamnosides from 6-thio mannosides

A. E. Christina, D. V. D. Es, J. Dinkelaar, H. S. Overkleeft, G. A. V. D. Marel and J. D. C. Codée, Chem. Commun., 2012, 48, 2686 DOI: 10.1039/C2CC17623H

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