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Determination of the Absolute Configuration of Dimethyl (2 S ,3 S )‐2‐Allyl‐3‐hydroxyglutarate: A Chiral Building Block for Preparing Branched‐Chain Nucleoside Analogues
Author(s) -
Arslan Tuncer,
Herradon Bernardo,
Schweizer Bernd W.,
Benner Steven A.
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760821
Subject(s) - chemistry , derivative (finance) , nucleoside , absolute configuration , stereochemistry , yeast , block (permutation group theory) , chain (unit) , biochemistry , financial economics , economics , physics , geometry , mathematics , astronomy
A yeast‐catalyzed reduction of dimethyl (2 S ,3 S )‐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.