Synthetic studies on an oligosaccharide of a glycolipid from the spermatozoa of bivalves IX. Syntheses of lipids I, II, and IV

✍ Scribed by Noriyasu Hada; Tadahiro Takeda; Yukio Ogihara

• Book ID: 102997671
• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 919 KB
• Volume: 258
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(94)84078-4

✦ Synopsis

Glycosphingolipids isolated from the spermatozoa of the freshwater bivalve, Hyriopsis ddegelii, have a unique structure containing one or two mannosyl residues and novel linkages, including an internal fucopyranosyl residue, as well as terminal xylosyl and 4-0-methyl-o-glucopyranosyluronic acid groups. The octasaccharide of lipid IV was synthesized as follows. Condensation of methyl (2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-methylcr-o-galactopyranosyl)-(l + 3)_[methy1~2,3-di-0-acetyl-4-O-methyl-P_nate)-(1 + 4)]-2-O-benzyl-l-thio-cQ+fucopyranoside (18) with (3-0-acetyl-6-0-benzyl-2-deoxy-2-phthalimido-/3-D-glucopyranosyl)-(1 + 2)_(3,4,6-tri-o-acetylyl-cu-D-mannopyranosyl)-(1 + 3)-[(2,3,4-tri-O-acetyl+o-xylopyranosyl)-(1 + 2)]_(4,6-di-o-acetyl-~-o-mannopyranosyl)~l + 4)_2,3-di-O-acetyl-1,6-anhydro-j3-o-glucopyranose (14), in the presence of dimethyl (methylthio) sulfonium triflate (DMTST), gave the corresponding octasaccharide (19).