✦ LIBER ✦

Epoxides of Phytosphingosine and Derivatives, Potential Inhibitors of Sphingosine Biosynthesis

✍ Scribed by Birk, Rolf ;Sandhoff, Konrad ;Schmidt, Richard R.

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 458 KB
Volume: 1993
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199319930112

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✦ Synopsis

Abstract

2,4‐O‐Benzylidene‐D‐threose (1) was treated with the Grignard reagent obtained from n‐octyl bromide to afford the epimeric tetrol derivatives 3a, b. Regioselective 2‐O‐mesylation and subsequent azido group introduction furnished azidophytosphingosine derivatives 5a, b. Ensuing 4‐O‐mesylation, acidcatalyzed benzylidene group removal and then treatment with NaH as a base provided preferentially the desired 3,4‐epoxide derivatives 8a, b; subsequent azido group reduction with triphenylphosphane/water yielded the target molecules 9a, b possessing D‐ribo and L‐lyxo configuration, respectively.

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