2-乙酰氨基-2-脱氧-3-O-β-D-岩藻糖基-α-D-吡喃半乳糖苷苄酯和2-乙酰氨基-6-O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-2-脱氧-3-O-β-D-岩藻糖基-α-D-吡喃半乳糖苷苄酯的合成
Synthesis of benzyl 2-acetamido-2-deoxy-3-O-beta-D-fucopyranosyl-alpha-D-galactopyranoside and benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-beta- D-glucopyranosyl)-2-deoxy-3-O-beta-D-fucopyranosyl-alpha-D- galactopyranoside.
作者信息
Piskorz C F, Abbas S A, Matta K L
出版信息
Carbohydr Res. 1984 Aug 15;131(2):257-63. doi: 10.1016/0008-6215(84)85247-7.
Condensation of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D- galactopyranoside with 2,3,4-tri-O-acetyl-alpha-D-fucopyranosyl bromide in 1:1 nitromethane-benzene, in the presence of powdered mercuric cyanide, afforded benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4-tri-O-acetyl-beta-D- fucopyranosyl)-alpha-D-galactopyranoside (3). Cleavage of the benzylidene group of 3 with hot, 60% aqueous acetic acid afforded diol 4, which, on deacetylation, furnished the disaccharide 5. Condensation of diol 4 with 2-methyl-(3,4,6-tri-O-acetyl-1,2-di-deoxy-alpha-D-glucopyrano)-[2, 1-d]-2- oxazoline in 1,2-dichloroethane afforded the trisaccharide derivative (7). Deacetylation of 7 with Amberlyst A-26 (OH-) anion-exchange resin in methanol gave the title trisaccharide (8). The structures of 5 and 8 were confirmed by 13C-n.m.r. spectroscopy.
在粉末状氰化汞存在下，将2-乙酰氨基-4,6-O-亚苄基-2-脱氧-α-D-吡喃半乳糖苄酯与2,3,4-三-O-乙酰基-α-D-吡喃岩藻糖基溴在1:1的硝基甲烷-苯中反应，得到2-乙酰氨基-4,6-O-亚苄基-2-脱氧-3-O-(2,3,4-三-O-乙酰基-β-D-吡喃岩藻糖基)-α-D-吡喃半乳糖苄酯(3)。用热的60%乙酸水溶液裂解3的亚苄基得到二醇4，4脱乙酰基后得到二糖5。二醇4与2-甲基-(3,4,6-三-O-乙酰基-1,2-二脱氧-α-D-吡喃葡萄糖基)-[2,1-d]-2-恶唑啉在1,2-二氯乙烷中反应得到三糖衍生物(7)。用甲醇中的Amberlyst A-26(OH-)阴离子交换树脂使7脱乙酰基得到标题三糖(8)。通过13C核磁共振光谱确定了5和8的结构。
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