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Synthesis of a precursor of 3-O-(2-acetamido-2-deoxy-3-O-methyl-α-d-galactopyranosyl)-4-O-(4-O-methyl-β-d-glucopyranosyluronic acid)-l-fucose

✍ Scribed by Osamu Kanie; Tadahiro Takeda; Yukio Ogihara

Publisher
Elsevier Science
Year
1989
Tongue
English
Weight
917 KB
Volume
190
Category
Article
ISSN
0008-6215

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✦ Synopsis

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-3-0methyl-cY-D-galactopyranosyl bromide with 2-(trimethylsilyl)ethyl 4-O-acetyl-2-0benzyl-/3-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-cu-D-glucopyranosyl bromide)uronate with the appropriate OH-Cfree disaccharide derivative afforded the corresponding precursor of 4-O-Me-&D-GlcpA-(1~4)-[3-O-Me-a-D-GalpNAc-(l~3)]-L-Fuc, namely 2-(trimethylsilyl)ethyl 2-0-benzyl-3-0-(4,6-di-O-acetyl-2-azido-2-deoxy-3-0-methyl-a-D-galactopyranosyll-4-0-[methyl (2,3-di-O-acctyl-4-O-methyl-P-Dglucopyranosyl)uronate]-/3-r_-fucopyranoside.

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