Matta K L, Barlow J J
Carbohydr Res. 1976 Nov;51(2):215-22. doi: 10.1016/s0008-6215(00)83328-5.
The use of the chloroacetyl group as a protecting group has been studied for a 2-methylglyco-[2',1':4,5]-2-oxazoline. The reaction of chloroacetyl chloride or chloroacetic anhydride with 2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-beta-D-glucopyranose provided 2-acetamido-1,3,4-tri-O-acetyl-6-O-(chloroacetyl)-2-deoxy-beta-D-glucopyranose which, on treatment with anhydrous ferric chloride in dichloromethane, produced the desired oxazoline. The glycosylating capability of the oxazoline has been investigated with aglycon hydroxides, to give the corresponding 2-acetamido-2-deoxy-beta-D-glucopyranosides. The chloroacetyl group can be selectively removed by treatment with thiourea, and migration of O-acetyl groups was not observed under these conditions.
已对氯乙酰基作为2-甲基糖基-[2',1':4,5]-2-恶唑啉的保护基的用途进行了研究。氯乙酰氯或氯乙酸酐与2-乙酰氨基-1,3,4-三-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖反应，得到2-乙酰氨基-1,3,4-三-O-乙酰基-6-O-(氯乙酰基)-2-脱氧-β-D-吡喃葡萄糖，该产物在二氯甲烷中用无水氯化铁处理后，生成所需的恶唑啉。已用糖苷配基氢氧化物研究了恶唑啉的糖基化能力，以得到相应的2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷。氯乙酰基可用硫脲处理选择性除去，在此条件下未观察到O-乙酰基的迁移。
