Matta K L, Barlow J J
Carbohydr Res. 1977 Jan;53(1):47-56. doi: 10.1016/s0008-6215(00)85453-1.
A simple synthesis of disaccharide oxazolines has been developed. Condensation of methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide, followed by removal of the 4,6-O-benzylidene group from the resulting disaccharide derivative, gave crystalline methyl 2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-glucpyranoside which, on acetolysis with acetic anhydride-acetic acid-sulfuric acid, provided 2-methyl-[4,6-di-O-acetyl-1,2-dideoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-glucopyrano]-[2',1':4,5]-2-oxazoline (7). Synthesis of the related alpha-D-mannopyranosyl compound was similarly accomplished. The glycosylating capability of 7 was employed for the synthesis of 6-(benzyloxycarbonylamino)hexyl-2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside (18). An alternative synthesis of compound 18 is also described.
已开发出一种简单的二糖恶唑啉合成方法。2-乙酰氨基-4,6-O-亚苄基-2-脱氧-α-D-吡喃葡萄糖苷甲酯与2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖基溴缩合，然后从所得二糖衍生物中除去4,6-O-亚苄基，得到结晶的2-乙酰氨基-2-脱氧-3-O-(2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基)-α-D-吡喃葡萄糖苷甲酯，其在用乙酸酐-乙酸-硫酸进行乙酰解时，得到2-甲基-[4,6-二-O-乙酰基-1,2-二脱氧-3-O-(2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基)-α-D-吡喃葡萄糖基]-[2',1':4,5]-2-恶唑啉(7)。相关的α-D-甘露糖基化合物的合成也以类似方式完成。利用7的糖基化能力合成了6-(苄氧羰基氨基)己基-2-乙酰氨基-4,6-二-O-乙酰基-2-脱氧-3-O-(2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基)-β-D-吡喃葡萄糖苷(18)。还描述了化合物18的另一种合成方法。
