Synthesis of a fully protected derivative of O-(N-acetyl-α-d-neuraminyl)-(2→3)-O-β-d-galactopyranosyl-(1→3)-O- [(N-acetyl-α-d-neuraminyl)-(2→6)]-O-(2-acetamido-2-deoxy-α-d-galactopyranosyl)-(1→3)-l-serine☆

Add time:08/16/2019    Source:sciencedirect.com

N-(Benzyloxycarbonyl)-O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5- dideoxy-d-glycero-α-d-galacto-2-nonulopyranosyl)onate]-(2→3)-O-(2,4,6-tri-O- acetyl-β-d-galactopyranosyl)-(1→3)-O-[methyl (5-acetamido-4,7,8,9-tetra-O- acetyl-3,5-dideoxy-d-glycero-α-d-galacto-2-nonulopyranosyl)onate-(2→6)]-O-(2- acetamido-4-O-acetyl-2-deoxy-α-d-galactopyranosyl)-(1→3)-l-serine benzyl ester was synthesized by using O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy- d-glycero-α-d-galacto-2-nonulopyranosyl)onate]-(2→3)-O-(2,4,6-tri-O-acetyl- β-d-galactopyranosyl)-(1→3)-O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl- 3,5-dideoxy-d-glycero-α-d-galacto-2-nonulopyranosyl)onate-(2→6)]-4-O-acetyl-2- azido-2-deoxy-α- and -β-d-galactopyranosyl trichloroacetimidate as a key glycotetraosyl donor which, upon reaction with N-(benzyloxycarbonyl)-l-serine benzyl ester, afforded a 44% yield of a mixture of the α- and β-glycosides in the ratio of 2:5.

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