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

M Morita; E Sawa; K Yamaji; T Sakai; T Natori; Y Koezuka; H Fukushima; K Akimoto

doi:10.1271/bbb.60.288

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

Biosci Biotechnol Biochem. 1996 Jan;60(2):288-92. doi: 10.1271/bbb.60.288.

Authors

M Morita¹, E Sawa¹, K Yamaji¹, T Sakai¹, T Natori¹, Y Koezuka¹, H Fukushima¹, K Akimoto¹

Affiliation

¹ a Pharmaceutical Research Laboratory, Kirin Brewery Co., Ltd., , 3 Miyahara-cho, Takasaki-shi, Gunma 370-12 , Japan.

PMID: 27299402
DOI: 10.1271/bbb.60.288

Abstract

A practical total synthesis of (2S,3S,4R)-l-O-(α-d-galactopyranosyl)-N-hexacosanoyl-2-amino-l,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.

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