Abstract
The glycosphingolipids isolated from spermatozoa of a fresh-water bivalve, Hyriopsis schlegelii, have a unique structure containing one or two mannosyl residues, novel linkages including an internal fucopyranosyl residue, as well as terminal xylosyl and 4-O-methyl-d-glucopyranosyluronic acid groups. The trisaccharide derivatives that constitute the partial structure of lipid IV were synthesized as follows. Condensation of 4,6-di-O-acetyl-2-azido-2-deoxy-3-O-methyl-α-d-galactopyranosyl bromide with 2-(trimethylsilyl)ethyl 4-O-acetyl-2-O-benzyl-β-l-fucopyranoside, in the presence of mercuric cyanide and mercuric bromide, gave the corresponding disaccharide in 87% yield. Condensation of methyl (2,3-di-O-acetyl-4-O-methyl-α-d-glucopyranosyl bromide)uronate with the appropriate OH-4-free disaccharide derivative afforded the corresponding precursor of 4-O-Me-β-d-GlcpA-(1→4)-[3-O-Me-α-d-GalpNAc-(1→3)]-l-Fuc, namely 2-(trimethylsilyl)ethyl 2-O-benzyl-3-O-(4,6-di-O-acetyl-2-azido-2-deoxy-3-O-methyl-α-d-galactopyranosyl]-4-O-[methyl (2,3-di-O-acetyl-4-O-methyl-β-d-glucopyranosyl)uronate]-β-l-fucopyranoside.
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