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-Galactosylceramide, KRN7000

Article abstract of DOI:10.1271/bbb.60.288

A practical total synthesis of (2S,3S,4A)-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.

Full text of DOI:10.1271/bbb.60.288

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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 Moritaa, Eiji Sawaa, Kazuo Yamajia, Teruyuki Sakaia, Takenori Natoria, Yasuhiko
Koezukaa, Hideaki Fukushimaa & Kohji Akimotoa
a Pharmaceutical Research Laboratory, Kirin Brewery Co., Ltd.,, 3 Miyahara-cho,
Takasaki-shi, Gunma 370–12, Japan
Published online: 12 Jun 2014.
To cite this article: Masahiro Morita, Eiji Sawa, Kazuo Yamaji, Teruyuki Sakai, Takenori Natori, Yasuhiko Koezuka, Hideaki
Fukushima & Kohji Akimoto (1996) 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, Bioscience,
Biotechnology, and Biochemistry, 60:2, 288-292, DOI: 10.1271/bbb.60.288
To link to this article: http://dx.doi.org/10.1271/bbb.60.288
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