3,6-二-O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-D-半乳糖的合成，该支链三糖被报道为血型物质的水解产物。
The synthesis of 3, 6-di-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-D-galactose, a branched trisaccharide reported as a hydrolysis product of blood-group substances.
作者信息
David S, Veyières A
出版信息
Carbohydr Res. 1975 Mar;40(1):23-9. doi: 10.1016/s0008-6215(00)82665-8.
PMID:1125950
Abstract
Protected disaccharides were the only products that could be isolated after condensation of 3, 4, 6-tri-O-acetyl-2-deoxy-2-diphenoxyphosphoramido-alpha-D-glucopyranosyl bromide or 2-acetamido-3, 4, 6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride with benzyl 2, 4-di-O-benzyl-beta-D-galactopyranoside. On the other hand, reaction of 2-methyl-(3, 4, 6-tri-O-acetyl-1, 2-dideoxy-alpha-D-glucopyrano)-[2', 1': 4, 5]-2-oxazoline (6 moles) with the same galactopyranoside (1 mole) gave benzyl 3, 6-di-O-(2-acetamido-3, 4, 6-tri-O-acetyl-beta-D-glucopyranosyl)-2, 4-di-O-benzyl-beta-D-galactopyranoside, which was converted, by alkaline methanolysis followed by hydrogenolysis, to the title compound. This appears identical with an oligosaccharide previously obtained through degredation of a blood-group A glycoprotein from hog gastric mucin.
摘要
在将3,4,6-三-O-乙酰基-2-脱氧-2-二苯氧基磷酰胺基-α-D-吡喃葡萄糖基溴或2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-α-D-吡喃葡萄糖基氯与苄基2,4-二-O-苄基-β-D-吡喃半乳糖苷缩合后，可分离得到的唯一产物是受保护的二糖。另一方面，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':4,5]-2-恶唑啉（6摩尔）与相同的吡喃半乳糖苷（1摩尔）反应，得到苄基3,6-二-O-(2-乙酰氨基-3,4,6-三-O-乙酰基-β-D-吡喃葡萄糖基)-2,4-二-O-苄基-β-D-吡喃半乳糖苷，通过碱性甲醇解然后氢解将其转化为标题化合物。这似乎与先前通过猪胃粘蛋白血型A糖蛋白降解得到的一种寡糖相同。
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The synthesis of 3, 6-di-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-D-galactose, a branched trisaccharide reported as a hydrolysis product of blood-group substances.3,6-二-O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-D-半乳糖的合成，该支链三糖被报道为血型物质的水解产物。
Carbohydr Res. 1975 Mar;40(1):23-9. doi: 10.1016/s0008-6215(00)82665-8.
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