Practical Total Synthesis of (2S, 3S, 4R)-1-O-(α-D-Galactopyranosyl)-N-hexacosanoyl-2-amino-1, 3, 4-octadecanetriol, the Antitumorial and Immunostimulatory α-Galactosylcer-amide, KRN7000

Masahiro MORITA; Eiji SAWA; Kazuo YAMAJI; Teruyuki SAKAI; Takenori NATORI; Yasuhiko KOEZUKA; Hideaki FUKUSHIMA; Kohji AKIMOTO

doi:10.1271/bbb.60.288

Masahiro MORITA, Eiji SAWA, Kazuo YAMAJI, Teruyuki SAKAI, Takenori NATORI, Yasuhiko KOEZUKA, Hideaki FUKUSHIMA, Kohji AKIMOTO

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Keywords: KRN7000, agelasphins, α-galactosylceramide, practical total synthesis, D-lyxose

JOURNAL FREE ACCESS

1996 Volume 60 Issue 2 Pages 288-292

DOI https://doi.org/10.1271/bbb.60.288

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Abstract

A practical total synthesis of (2S, 3S, 4R)-1-O-(α-D-galactopyranosyl)-N-hexacosanoyl-2-amino-1, 3, 4-octadecanetriol (KRN7000), an antitumorial and immunostimulatory glycosphingolipid derived from agelasphins, was achieved in 14 steps starting from D-lyxose in a 16% overall yield.

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