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Synthesis 2005(13): 2267-2269  
DOI: 10.1055/s-2005-869986
PSP
© Georg Thieme Verlag Stuttgart · New York

Convenient Enantiopure Synthesis of (2S,3R)-2-O-Benzyl-3,4-O-isopropylidene-d-erythritol from d-(+)-Glucono-δ-lactone: A Potential C4 Chiral Building Block

Sivalenka Vijayasaradhi, Manjunath Narayana Beedimane, Indrapal Singh Aidhen*
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India
Fax: +91(44)22578241; e-Mail: isingh@iitm.ac.in;
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Publication History

Received 24 November 2004
Publication Date:
27 June 2005 (online)

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Abstract

A new convenient synthesis of (2S,3R)-2-O-benzyl-3,4-O-isopropylidene-d-erythritol has been achieved starting from extremely cheap and commercially available d-(+)-glucono-δ-lactone. It involves two carbon excisions using ozonolysis. The inbuilt stereochemistry ensures the enantiopurity of the target compound.

Key words

lactones - eliminations - ozonolysis - reduction