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Updated: Aug 13, 2026

A Strategy for Sensitive, Large Scale Quantitative Metabolomics
Published on: May 27, 2014
Diastereoselective synthesis of all eight l-hexoses from L-ascorbic acid
Ludmila Ermolenko1, N André Sasaki
1Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Abstract:
[reaction: see text] A novel versatile method for the synthesis of all eight diastereomerically pure L-hexoses was developed. L-Ascorbic acid was converted to two diastereomers A. These alpha-hydroxy esters were transformed into four gamma-alkoxy-alpha,beta-unsaturated esters C via the intermediates B and subsequent Wittig olefination reactions. Each one of compounds C was subjected to dihydroxylation to provide a set of two diols D. Anti/syn-differentiation in diol formation was manipulated by using (DHQD)2PHAL and (DHQ)2PHAL as chiral ligands. Further two-step reaction sequence affords all eight diastereopure L-hexoses.
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