Issue 5, 2009
From the journal:

Organic & Biomolecular Chemistry

Developing an asymmetric, stereodivergent route to selected 6-deoxy-6-fluoro-hexoses†

Audrey Caravano,a   Robert A. Field,b   Jonathan M. Percy,*c   Giuseppe Rinaudo,c   Ricard Roiga  and  Kuldip Singha  

* Corresponding authors

a Department of Chemistry, University of Leicester, University Road, Leicester, UK

b Department of Biological Chemistry, John Innes Centre, Colney Lane, Norwich

c WestCHEM Department of Pure and Applied Chemistry, Thomas Graham Building, 295 Cathedral Street, Glasgow, UK
E-mail: jonathan.percy@strath.ac.uk
Fax: +44 141 4822
Tel: +44 141 548 4398

Abstract

Free radical bromination and nucleophilic fluorination allows the conversion of methyl sorbate into the 6-fluoro analogue which undergoes sequential asymmetric dihydroxylation reactions. A range of 6-deoxy-6-fluorosugars were prepared by using different combinations of ligands. While the enantiomeric excesses obtained were comparable to those from other 6-substituted sorbates, the regioselectivity of dihydroxylation was moderate, with both 2,3- and 4,5-diols being obtained. A successful temporary persilylation strategy was evolved to convert the products of dihydroxylation rapidly to the fluorosugars 6-deoxy-6-fluoro-L-idose, 6-fluoro-L-fucose and 6-deoxy-6-fluoro-D-galactose, which were obtained in overall yields of 4%, 6% and 8% from methyl 6-fluoro-hexa-2E,4E-dienoate 6.

Graphical abstract: Developing an asymmetric, stereodivergent route to selected 6-deoxy-6-fluoro-hexoses

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B815342F
Article type
Paper
Submitted
03 Sep 2008
Accepted
11 Dec 2008
First published
23 Jan 2009

Org. Biomol. Chem., 2009,7, 996-1008

Permissions

Request permissions

Developing an asymmetric, stereodivergent route to selected 6-deoxy-6-fluoro-hexoses

A. Caravano, R. A. Field, J. M. Percy, G. Rinaudo, R. Roig and K. Singh, Org. Biomol. Chem., 2009, 7, 996 DOI: 10.1039/B815342F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements