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http://dx.doi.org/10.5012/bkcs.2009.30.3.695

Stereoselective Transformation of Phytosphingosine to Safingol  

Kim, Na-Ri (Department of Chemistry, Seoul Women’s University)
Lee, Sun-Hee (Department of Chemistry, Seoul Women’s University)
Namgoong, Sung-Keon (Department of Chemistry, Seoul Women’s University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.3, 2009 , pp. 695-699 More about this Journal
Abstract
A short and efficient synthesis of (2S,3S)-safingol from commercially available D-ribo-(2S,3S,4R)-phytosphingosine is described. The highlights of the synthesis are a stereoselective one-pot transformation of a diol into an epoxide under phase transfer catalytic conditions and a regioselective epoxide-opening reduction with a hydride reagent.
Keywords
Safingol; Phytosphingosine,; Phase transfer catalysis,; Epoxide-forming reaction; Reduction;
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