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Issue 1, 1989
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Enantiospecific syntheses of the methylene-and α-fluoromethylene-phosphonate analogues of 3-phospho-D-glyceric acid

Abstract

An enantioselective synthesis is described for the preparation of 2-(R)-3-carboxy-3-hydroxypropane-1-phosphonic acid (1), an isosteric analogue of 3-phospho-D-glyceric acid (2), from D-lyxose; the route is extended to provide a stereoselective synthesis of one diastereoisomer of 2-(R)-3-carboxy-1-fluoro-3-hydroxypropane-1-phosphonic acid (3), of undetermined stereochemistry at C-1; these preparations provide the first examples of syntheses of phosphonate analogues of 3-phospho-D-glyceric acid having the natural configuration at C-2.

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Article information


J. Chem. Soc., Chem. Commun., 1989, 40-41
Article type
Paper

Enantiospecific syntheses of the methylene-and α-fluoromethylene-phosphonate analogues of 3-phospho-D-glyceric acid

G. M. Blackburn and A. Rashid, J. Chem. Soc., Chem. Commun., 1989, 40
DOI: 10.1039/C39890000040

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