Synthesis 2004(18): 2991-2994  
DOI: 10.1055/s-2004-834889
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of l-Pyranosides from 5-Enopyranosides by Diastereoselective Hydroboration/Oxidation

Hideyo Takahashi, Namisa Miyama, Haruhiko Mitsuzuka, Shiro Ikegami*
Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa 199-0195, Japan
Fax: +81(426)853729; e-Mail: shi-ike@pharm.teikyo-u.ac.jp;
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Publikationsverlauf

Received 2 August 2004
Publikationsdatum:
22. Oktober 2004 (online)

Abstract

Improved synthesis of l-pyranosides utilizing diastereoselective hydroboration/oxidation of 5-enopyranosides was investigated. A unique phenomenon in the diastereoselectivity of the hydroboration was incidentally found. The method was successfully applied to the synthesis of l-iduronic acid.

11

Other reaction conditions (e.g., temperature, time, and solvent) were not changed.

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Compound 2a was easily separated from 3a using chromatography on silica gel.