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目的设计合成博来霉素二糖新型前体化合物。方法以廉价易得的D-甘露糖为原料,以最短直线步骤6步实现了新型甘露糖砌块乙硫基-2-O-乙酰基-3-O-氨基甲酰基-4,6-O-苄叉基-α-D-吡喃甘露糖苷(3)的合成;以廉价易得的甲基-α-D-吡喃葡萄糖苷为原料,经13步反应得到了新型古洛糖砌块对甲苯硫基-2-O-羟基-3,4,6-三-O-苄基-α,β-L-吡喃古洛糖苷(4),两个单糖砌块经糖苷化反应得到了博来霉素二糖的前体化合物对甲苯硫基-3,4,6-三-O-苄基-2-O-(2-乙酰基-3-氨基甲酰基-4,6-苄叉基-α-D-吡喃甘露糖基))-α,β-L-吡喃古洛糖(2)。结果与结论实现了新型甘露糖砌块3和新型古洛糖砌块4的合成,反应总收率分别为28%和8%;经糖苷化反应得到了博来霉素二糖前体化合物2,反应收率达83%。所有合成的新化合物均经过IR,1H-NM R,13C-NM R和HRM S进行表征。
OBJECTIVE To design a new bleomycin disaccharide novel precursor compound. Methods Starting from cheap and readily available D-mannose, the novel mannose block ethylthio-2-O-acetyl-3-O-carbamoyl-4,6-O -benzylidene-α-D-mannopyranoside (3). A novel gulo sugar block was obtained from 13-step reaction of methyl-α-D-glucopyranoside, P-Tolylthio-2-O-hydroxy-3,4,6-tri-O-benzyl-α, β-L-pyroglucose glycoside (4) P-Tolylthio-3,4,6-tri-O-benzyl-2-O- (2-acetyl-3-carbamoyl-4,6-benzyl Α-D-mannopyranosyl)) - α, β-L-pyrogulose (2). RESULTS AND CONCLUSIONS The synthesis of novel mannose block 3 and novel gulnut block 4 were achieved with total yields of 28% and 8%, respectively. The results of glycosylation indicated that bleomycin disaccharide precursor compound 2 , The reaction yield of 83%. All new compounds synthesized were characterized by IR, 1H-NM R, 13C-NM R and HRM S.