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 | Zendy

Arslan Tuncer | Zendy; Herradon Bernardo | Zendy; Schweizer Bernd W. | Zendy; Benner Steven A. | Zendy

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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.

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