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Issue 5, 2009
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Developing an asymmetric, stereodivergent route to selected 6-deoxy-6-fluoro-hexoses

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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

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Supplementary files

Article information


Submitted
03 Sep 2008
Accepted
11 Dec 2008
First published
23 Jan 2009

Org. Biomol. Chem., 2009,7, 996-1008
Article type
Paper

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

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