Synthesis of a hematoside analog containing phytosphingosine and α-hydroxfatty acid

Tetsuji Sugata, Yoko Kan, Yoshiteru Nagaregawa, Tomofumi Miyamoto, Ryuichi Higuchi

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The hematoside analog 1 [NeuGcα(2→3)Galβ(1→4)Glcβ(1→1)Cer], which contains a phytosphingosine as a sphingoid base and an α-hydroxyfatty acid, has been synthesized. Coupling of the methyl (methyl 5-benzyloxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero- α-and -β-D-galacto-2-nonulopyranosid)onate 5, prepared from the corresponding 5-acetamido derivative 2, with a lactose derivative 6 afforded sialolactoside 7, which was converted to the corresponding trichloroacetimidate 10. Glycosylation of 10 with the ceramide tribenzoate 12 gave the protected hematoside analog 13, which was deprotected to the hematoside analog 1.

Original languageEnglish
Pages (from-to)917-925
Number of pages9
JournalJournal of Carbohydrate Chemistry
Volume16
Issue number6
DOIs
Publication statusPublished - Jan 1 1997

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phytosphingosine
G(M3) Ganglioside
Acids
Derivatives
Glycosylation
Ceramides
Lactose

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

Cite this

Synthesis of a hematoside analog containing phytosphingosine and α-hydroxfatty acid. / Sugata, Tetsuji; Kan, Yoko; Nagaregawa, Yoshiteru; Miyamoto, Tomofumi; Higuchi, Ryuichi.

In: Journal of Carbohydrate Chemistry, Vol. 16, No. 6, 01.01.1997, p. 917-925.

Research output: Contribution to journalArticle

Sugata, Tetsuji ; Kan, Yoko ; Nagaregawa, Yoshiteru ; Miyamoto, Tomofumi ; Higuchi, Ryuichi. / Synthesis of a hematoside analog containing phytosphingosine and α-hydroxfatty acid. In: Journal of Carbohydrate Chemistry. 1997 ; Vol. 16, No. 6. pp. 917-925.
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