Total synthesis of 3-O-[2-acetamido-6-O-(N-acetyl-α-d

Add time:08/07/2019    Source:sciencedirect.com

O-(5-Acetamido-3,5-dideoxy-d-glycero-α-d-galacto-2-nonulopyranosylonic acid)-(2→6)-O-(2-acetamido-2-deoxy-α-d-galactopyranosyl)-(1→3)-l-serine, a structural unit occurring in various submaxillary mucins, was synthesized for the first time 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→6)-3,4-di-O-acetyl-2- azido-2-deoxy-d-galactopyranosyl trichloroacetimidate (13) and N-(benzyloxycarbonyl)-l-serine benzyl ester as the key intermediates. The trichloroacetimidate 13 was prepared by starting from two monosaccharide synthons, namely, ally 2-azido-2-deoxy-β-d-galactopyranoside and methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-d-glycero-β-d-galacto-2-nonulopyranosyl chloride)onate, which were coupled in the presence of silver triflate in tetrahydrofuran to give the desired α-(2→6)-linked disaccharide in moderate selectivity.

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