对三氟乙酰氨基苯基 O-α-D-甘露吡喃糖基-(1→3)-O-[α-D-甘露吡喃糖基-(1→6)]-β-D-甘露吡喃糖苷

p-Trifluoroacetamidophenyl O-alpha-D-mannopyranosyl-(1----3)-O-[alpha-D-mannopyranosyl- (1----6)]-beta-D-mannopyranoside.

作者信息

Ekborg G, Glaudemans C P

出版信息

Carbohydr Res. 1985 Oct 15;142(2):213-21. doi: 10.1016/0008-6215(85)85024-2.

Abstract

p-Nitrophenyl 2-O-benzyl-4,5-O-cyclohexylidene-beta-D-mannopyranoside (4) was condensed with tetra-O-benzoyl-alpha-D-mannopyranosyl bromide. The resulting, protected disaccharide was converted into p-nitrophenyl O-(2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl)-(1----3)-4-O-benzoyl-2-O- benzyl-beta-D-mannopyranoside (8), which was condensed with tetra-O-benzoyl-alpha-D-mannopyranosyl bromide to give p-nitrophenyl O-(2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl)-(1----3)-O -[2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl-(1----6)]-4-O-benzoyl-2-O -benzyl-beta-D-mannopyranoside (9) in 75% yield. Conversion of the p-nitrophenyl group followed by deprotection then yielded the title compound, whose structure was confirmed by 1H- and 13C-n.m.r. spectroscopy.

摘要

对硝基苯基 2-O-苄基-4,5-O-环己叉基-β-D-甘露吡喃糖苷（4）与四-O-苯甲酰基-α-D-甘露吡喃糖基溴进行缩合反应。所得的保护二糖被转化为对硝基苯基 O-(2,3,4-三-O-苯甲酰基-α-D-甘露吡喃糖基)-(1→3)-4-O-苯甲酰基-2-O-苄基-β-D-甘露吡喃糖苷（8），其与四-O-苯甲酰基-α-D-甘露吡喃糖基溴缩合，以 75%的产率得到对硝基苯基 O-(2,3,4-三-O-苯甲酰基-α-D-甘露吡喃糖基)-(1→3)-O-[2,3,4-三-O-苯甲酰基-α-D-甘露吡喃糖基-(1→6)]-4-O-苯甲酰基-2-O-苄基-β-D-甘露吡喃糖苷（9）。对硝基苯基的转化随后进行脱保护，得到标题化合物，其结构通过 1H-和 13C-核磁共振光谱得到证实。