Determination of the Absolute Configuration of Dimethyl (2S,3S)-2-Allyl-3-hydroxyglutarate: A Chiral Building Block for Preparing Branched-Chain Nucleoside Analogues

A yeast-catalyzed reduction of dimethyl (2S,3S)-2-allyl-3-hydroxyglutarate is the key step in the preparation of bis-homo, branched-chain nucleoside analogues. To establish unambiguously the stereochemical course of the microbial reaction, the product has been converted to a derivative esterified with camphanoyl chloride, and a crystal structure of the derivative solved.