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.
M Morita  1 ,  E Sawa  1 ,  K Yamaji  1 ,  T Sakai  1 ,  T Natori  1 ,  Y Koezuka  1 ,  H Fukushima  1 ,  K Akimoto  1
Affiliations
  • 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.
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