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为了优化和改进糖苷化反应的合成工艺,首先以β-D-葡萄糖为原料,经乙酰化、溴代反应合成了糖供体2,3,4,6-O-四乙酰基-α-D-溴代葡萄糖(Ⅲ);再与2-羟基-3,4-二甲氧基苯甲醛(Ⅳ)经糖苷化反应合成了2,3,4,6-O-四乙酰基-(2,3-二甲氧基-6-甲酰基)苯基-β-D-葡萄糖苷(Ⅴ);最后对化合物Ⅴ进行水解得到了目标化合物(2,3-二甲氧基-6-甲酰基)苯基-β-D-葡萄糖苷(Ⅵ)。结果表明:在合成氧糖苷(Ⅴ)的过程中,采用无水K_2CO_3为缚酸剂,四丁基溴化铵(TBAB)为相转移催化剂,反应收率可达78.9%;化合物Ⅴ水解的最优条件是以甲醇为溶剂、无水K_2CO_3为催化剂。所得到产物经核磁、红外、质谱表征,证明为目标化合物。
In order to optimize and improve the synthesis process of glycosylation reaction, the sugar donor 2,3,4,6-O-tetraacetyl-α-D was synthesized from β-D-glucose by acetylation and bromination reaction Bromo-glucose (Ⅲ) was synthesized and then 2,3,4,6-O-tetraacetyl- (2, 3-dimethoxybenzaldehyde) was synthesized via glycosylation with 2-hydroxy- 3-dimethoxy-6-formyl) phenyl-β-D-glucoside (V). Finally, compound V is hydrolyzed to obtain the target compound (2,3- Phenyl-β-D-glucoside (Ⅵ). The results showed that anhydrous K 2 CO 3 as acid-binding agent and tetrabutyl ammonium bromide (TBAB) as phase-transfer catalyst could yield 78.9% of the total yield of the glycosides (Ⅴ) Excellent conditions are methanol as solvent, anhydrous K 2 CO 3 catalyst. The obtained product was characterized by NMR, IR and MS and proved to be the target compound.