具有生物学意义的模型寡糖的合成。3,6-二-O-(α-D-甘露吡喃糖基)-α-D-甘露吡喃糖苷甲酯及相应甘露二糖苷的合成。
Syntheses of model oligosaccharides of biological significance. Synthesis of methyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-d-mannopyranoside and the corresponding mannobiosides.
作者信息
Winnik F M, Brisson J R, Carver J P, Krepinsky J J
出版信息
Carbohydr Res. 1982 May 1;103(1):15-28. doi: 10.1016/s0008-6215(82)80004-9.
Methyl 2-O-allyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl) -alpha-D-mannopyranoside (12) was prepared in 90% yield by Helferich glycosylation of methyl 2-O-allyl-4,6-O-benzylidene-alpha-D-mannopyranoside (9) with tetra-O-acetyl-alpha-D-mannopyranosyl bromide (11). Removal of the benzylidene group and second Helferich glycosylation with 11 led to methyl 2-O-allyl-3,6-di-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (14) which, after deallylation and Zemplén deacetylation, gave the title compound 5. The disaccharides methyl 3-O-(alpha-D-mannopyranosyl)-alpha-mannopyranoside (7) and methyl 6-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (6) have also been synthesized. Complete assignments of the 1H-n.m.r. spectra of the compounds 5, 6, and 7 are given.
通过2-O-烯丙基-4,6-O-亚苄基-α-D-甘露吡喃糖苷（9）与四-O-乙酰基-α-D-甘露吡喃糖基溴（11）进行黑尔费里希糖基化反应，以90%的产率制备了2-O-烯丙基-4,6-O-亚苄基-3-O-(2,3,4,6-四-O-乙酰基-α-D-甘露吡喃糖基)-α-D-甘露吡喃糖苷（12）。去除亚苄基并再次用11进行黑尔费里希糖基化反应，得到2-O-烯丙基-3,6-二-O-(2,3,4,6-四-O-乙酰基-α-D-甘露吡喃糖基)-α-D-甘露吡喃糖苷（14），该化合物在脱烯丙基和泽普伦脱乙酰反应后，得到标题化合物5。还合成了二糖3-O-(α-D-甘露吡喃糖基)-α-甘露吡喃糖苷甲基酯（7）和6-O-(α-D-甘露吡喃糖基)-α-D-甘露吡喃糖苷甲基酯（6）。给出了化合物5、6和7的¹H-核磁共振谱的完整归属。
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