Diastereoselective epoxidation of the double bond at C-4 of sphingosines to provide phytosphingosine relatives such as α-galactosylceramide KRN7000
1998; Elsevier BV; Volume: 54; Issue: 13 Linguagem: Inglês
10.1016/s0040-4020(98)00065-9
ISSN1464-5416
AutoresHirosato Takikawa, Shin‐etsu Muto, Kenji Mori,
Tópico(s)Bioactive Compounds and Antitumor Agents
ResumoDiastereoselective epoxidation of the double bond at C-4 of two sphingosine derivatives [3, R = (CH2)7Me or (CH2)12Me] was studied. Dimethyldioxirane was found to be the best oxidant for that purpose. Application of this epoxidation resulted in a new synthesis of the α-galactosylceramide KRN7000 (2), which has an enhancing effect on the activity of natural killer cells.
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