4-硝基-1-萘基-β-D-半乳糖苷的合成研究

Synthesis of 4-nitro-1-naphthyl-β-D-galactopyranoside

目的设计合成4-硝基-1-萘基-β-D-半乳糖苷的方法。方法D-半乳糖与乙酸钠反应,酯化后得到β-D-半乳糖五乙酸酯。β-D-半乳糖五乙酸酯经过溴化氢的乙酸溶液溴代得到溴代糖、再用显色团4-硝基-1-萘酚取代端基溴、最终水解除去乙酰基,再重结晶得到目标化合物。对该目标化合物进行核磁共振(^(1)H-NMR、^(13)C-NMR)和高分辨质谱(ESI-HRMS)表征确定结构。对溴代试剂选择、羟基乙酰化反应条件及重结晶条件进行优化筛选。结果表征结果显示,终产物即为化合物4-硝基-1-萘基-β-D-半乳糖苷。制备过程中溴代试剂应选择溴化氢的乙酸溶液,乙酰化反应条件应选择反应温度130℃,反应时间3 h,重结晶甲醇/水比例为3∶1。结论应用本法合成目标化合物4-硝基-1-萘基-β-D-半乳糖苷,建立的反应条件温和,操作简便可行。

Objective Design and synthesis of 4-nitro-1-naphthyl-β-D-galactopyranoside.Methods D-galactose reacted with sodium acetate and was obtained after esterificationβ-D-galactose pentaacetate.β-D-galactose pentaacetate was subjected to hydroacetic acid bromide solution,substituted with chromophore 4-nitro-1-naphthol,final hydrolysis to remove acetyl group,and then recrystallized to obtain the target compound.The target compounds were characterized by nuclear magnetic resonance(^(1)H-NMR,^(13)C-NMR)and high resolution mass spectrometry(ESI-HRMS).The selection of brominated reagents,hydroxyl acetylation reaction conditions and recrystallization conditions were optimized.Results The characterization results showed that the end product was compound 4-nitro-1-naphthyl-β-D-galactopyranoside.In the preparation process,acetic acid solution of hydrogen bromide shall be selected as the brominating reagent,the reaction temperature should be 130℃and the reaction time should be 3 h,the ratio of recrystallized methanol/water shall be 3∶1.Conclusion The target compound 4-nitro-1-naphthyl-β-D-galactopyranoside was synthesized by this method and synthesis process is mild in reaction conditions and simple in operation.