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

DOI: 10.1016/S0040-4020(98)00065-9

Source and publish data:

Tetrahedron p. 3141 - 3150 (1998)

Update date:2022-09-26

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Authors:

Takikawa, Hirosato

Muto, Shin-etsu

Mori, Kenji

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Article abstract of DOI:10.1016/S0040-4020(98)00065-9

Diastereoselective 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.

Full text of DOI:10.1016/S0040-4020(98)00065-9

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