Diastereoselective epoxidation of the double bond at C-4 of sphingosines to provide phytosphingosine relatives such as α-galactosylceramide KRN7000

✍ Scribed by Hirosato Takikawa; Shin-etsu Muto; Kenji Mori

• Book ID: 104208457
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 746 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)00065-9

✦ Synopsis

Diastereoselcctive epoxidation of the double bond at C-4 of two sphingosine derwat1ve.r [J, R = (CHzhMe or (CH2)t2Me] was studied. Dimcthyldioxirane was found to be the best oxidant for that purpose. Application of this epoxidation resulted in a new synthesis of the a-galactosylceramidr KRN7000 (2). which has an enhancing effect on the activity of natural killer cells.