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

Article abstract of DOI:10.1080/07328309708006548

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.

Full text of DOI:10.1080/07328309708006548

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Journal of Carbohydrate Chemistry
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Synthesis of a Hematoside Analog
Containing Phytosphingosine and α-
Hydroxyfatty Acid
Tetsuji Sugata a , Yoko Kan a , Yoshiteru Nagaregawa a , Tomofumi
Miyamoto a & Ryuichi Higuchi a
a Faculty of Pharmaceutical Sciences, Kyushu University , Maidashi
3-1-1, Higashi-ku, Fukuoka, 812-82, Japan
Published online: 21 Aug 2006.
To cite this article: Tetsuji Sugata , Yoko Kan , Yoshiteru Nagaregawa , Tomofumi Miyamoto & Ryuichi
Higuchi (1997) Synthesis of a Hematoside Analog Containing Phytosphingosine and α-Hydroxyfatty
Acid, Journal of Carbohydrate Chemistry, 16:6, 917-925
To link to this article: http://dx.doi.org/10.1080/07328309708006548
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