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首次报道了苯丙素苷类化合物EutigosideA,即1-O-[2-(4-羟基苯基)乙基]-6-O-(E)-香豆酰基-β-D-吡喃葡萄糖的全合成.从四乙酰溴代葡萄糖出发,经过成苷、脱乙酰基两步反应,制备了2-对烯丙氧基苯基-β-D-吡喃葡萄糖苷(3),采用酰氯法在低温下将对乙酰氧基肉桂酰基引入化合物3的葡萄糖6位,再经过脱烯丙基、脱乙酰基两步,便顺利地合成了天然苯丙素苷Eutigoside A.以化合物3为原料,经过对葡萄糖4,6位亚苄基化、2,3位乙酰化、4,6位脱亚苄基、选择性6位乙酰化及4位引入对乙酰氧基肉桂酰基等五步反应,得到了保护的苯丙素苷Osmanthuside A(10);但在NH_3/MeOH条件下脱乙酰基时,化合物10中的香豆酰基从葡萄糖的4位迁移至6位,最终又得到了Eutigoside A.
The first report of the combination of the phenylpropanoid glycosides Eutigoside A, 1-O- [2- (4-hydroxyphenyl) ethyl] -6-0- (E) -coumaryl-β-D-glucopyranose Synthesis of 2-p-Allyloxyphenyl-β-D-glucopyranoside (3) was prepared from tetraacetylglucose by two steps of glycoside and deacetylation At low temperature, the acetoxy cinnamoyl group was introduced into 6 of glucose of compound 3, then deprotected and deacetylated, the natural phenylpropanoid Eutigoside A was successfully synthesized. After compound 3 was used as raw material, The five-step reaction of 4, 6-position benzylation of glucose, 2,3-acetylation, 4,6-debenzylidene, 6-position selective acetylation and 4-position introduction of p-acetoxycinnamoyl group gave the Protected phenylpropanoid Osmanthuside A (10); However, when deacetylated under NH 3 / MeOH conditions, the coumaroyl group in compound 10 migrated from the 4-position of glucose to the 6-position to finally obtain Eutigoside A again.