Synthetic Studies on Oligosaccharide of a Glycolipid from the Spermatozoa of Bivalves. VII. The Synthesis of Di-, Tri-, Tetrasaccharides Related to Glycosphingolipid

The three kinds of oligosaccharides that constitute the partial structure of lipid IV (1) were synthesized as follows. The disaccharide 0-β-D-mannopyranosyl-(l-→4)-D-glucopyranose (13), the trisaccharide O-α-D-mannopyranosyI-(l-→3)-0-β-D-mannopyranosyl-(l→4)-D-glucopyranose (21), and the tetrasaccharide 0-α-D-mannopyranosyl-(l-→3)~0-[β-D-xylopyranosyl-(l-→2)]-0β-D-mannopyranosyl-(l-»4)-D-glucopyranose (25) were each synthesized by stepwise condensation of suitably protected monosaccharide units. A 1,6-anhydro-D-glucopyranose derivative was used as the glycosyl acceptor, and bromide derivatives of D-mannose and D-xylose as donors.