Synthetic studies on selectin ligands/inhibitors: A systematic sysnthersis of sulfatide and its higher congeners carrying 2-(tetradecyl)hexadecyl group as a ceramide substitute

Article abstract of DOI:10.1080/07328309708006543

A systematic synthesis of sulfatide (I) and novel sulfatide analogs (II-VI) carrying 2-(tetradecyl)hexadecyl group as a ceramide substitute is described. The 3-O-, 4-O-and 3,4-di-O-levulinoyl derivatives of galactopyranosyl trichloroacetimidates (1, 12, and 13) were coupled with (2S,3R,4E)-3-O-acetyl-2-octadecanamido-4-octadecene-1,3-diol or 2-(tetradecyl)hexadecan-1-ol. The resulting glycolipids (2, 4, 14, and 15) were each transformed, by selective removal of the levulinoyl group(s), and successive sulfation and de-O-acylation, into the 3-sulfates (I, II), 4-sulfate (III), and 3,4-disulfate (IV). The 6-sulfate (V) was prepared from 2-(tetradecyl)hexadecyl β-D-galactopyranoside (21) via the 6-0-t-butyldimethylsilyl derivative, while the 3'-sulfate of 2-(tetradecyl)hexadecyl β-D-lactoside (VI) was synthesized from 2-(trimethylsilyl)ethyl 3'-O-benzyl-β-D-lactoside (26). The structures of the sulfated glycolipids (I-VI) were characterized by ion-spray MS, MS/MS, and ¹H NMR spectrometry.

Full text of DOI:10.1080/07328309708006543

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Synthetic Studies on Selectin Ligands/
Inhibitors: A Systematic Synthesis of
Sulfatide and Its Higher Congeners
Carrying 2-(Tetradecyl)Hexadecyl Group
as a Ceramide Substitute
Eiji Tanahashi a , Katsutoshi Murase a , Mika Shibuya a , Yumie
Igarashi a , Hideharu Ishida a , Akira Hasegawa a & Makoto Kiso a
a Department of Applied Bioorganic Chemistry , Gifu University ,
Gifu, 501-11, Japan
Published online: 21 Aug 2006.
To cite this article: Eiji Tanahashi , Katsutoshi Murase , Mika Shibuya , Yumie Igarashi , Hideharu
Ishida , Akira Hasegawa & Makoto Kiso (1997) Synthetic Studies on Selectin Ligands/Inhibitors: A
Systematic Synthesis of Sulfatide and Its Higher Congeners Carrying 2-(Tetradecyl)Hexadecyl Group as
a Ceramide Substitute , Journal of Carbohydrate Chemistry, 16:6, 831-858
To link to this article: http://dx.doi.org/10.1080/07328309708006543
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