A convenient synthesis of S-glycosyl donors of sialic acid and their use for O-glycosylation

Article abstract of DOI:10.1016/0008-6215(90)80045-5

Sialic acid S-glycosyl donors were prepared efficiently in one step by use of S,S'-bis(1-phenyl-1H-tetrazol-5-yl)dithiocarbonate (2) and used for O-glycosylation.The reaction of 2 with methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonate gave methyl <1-phenyl-1H-tetrazol-5-yl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α- (4) and -β-D-galacto-2-nonulopyranosid>onate (5), and 1-phenyl-1H-tetrazol-5-yl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranoside)thionate.Compounds 4 and 5 could be applied to the synthesis of a sialosyl-(2->6')-lactose derivative and cholester-3-yl sialoside, respectively.