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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 3
BKCSDE 30(3)
March 20, 2009 

 
Title
Stereoselective Transformation of Phytosphingosine to Safingol
Author
Nari Kim, Sun Hee Lee, Sung Keon Namgoong*
Keywords
Safingol, Phytosphingosine, Phase transfer catalysis, Epoxide-forming reaction, Reduction
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.
Page
695 - 699
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