Synthesis of p-nitrophenyl 3-O-β-d-galactopyranosyl-β-d-galactopyranoside and p-nitrophenyl 3-O-α-d-galactopyranosyl-β-d-galactopyranoside
作者:Saeed A. Abbas、Joseph J. Barlow、Khushi L. Matta
DOI:10.1016/s0008-6215(00)81003-4
日期:1982.3
3:1. The structures of 4 , 6 , 8 , and 10 were evidenced by their respective 1 H-n.m.r. spectra. O -Deacetylation of 4 and 6 afforded, respectively, p -nitrophenyl 3- O -α- d -galactopyranosyl-β- d -galactopyranoside ( 5 ) and p -nitrophenyl 3- O -β- d -galactopyranosyl-β- d -galactopyranoside ( 7 ). O -Deacylation of 8 and 10 furnished the disaccharide derivatives ( 9 and 11 ). Cleavage of the benzylidene
摘要对硝基苯基2,4,6-三-O-乙酰基-β-d-吡喃半乳糖苷(2)与2,3,4,6-四-O-乙酰基-α-d的糖基化反应(氰化汞催化)在乙腈中的-半乳糖基吡喃糖基溴化物以几乎相等的比例提供α-(1→3)-和β-(1→3)连接的二糖七乙酸酯(分别为4和6)。对-硝基苯基2-O-苯甲酰基-4,6-O-亚苄基-β-d-吡喃半乳糖苷(3)的类似糖基化反应产生了β-(1→3)-和α-(1→3)-相连,以3:1的比例完全保护的二糖衍生物(分别为8和10)。4,6,8和10的结构由它们各自的1 Hn.mr光谱证明。4和6的O-脱乙酰基分别提供对-硝基苯基3- O-α-d-吡喃半乳糖基-β-d-吡喃半乳糖苷(5)和对-硝基苯基3- O-β-d-吡喃半乳糖基-β-d-半乳糖吡喃糖苷(7)。8和10的O-脱酰作用提供了二糖衍生物(9和11)。9和11的亚苄基的切割分别给出了二糖7和5。5,7,9和11的结构是通过13