Synthesis of 4-nitro-1-naphthyl-β-D-galactopyranoside
DANG Jizheng1 YI Li2▲
1.Department of Pharmacy,Unisersity-Town Hospital of Chongqing Medical University,Chongqing 401331,China;
2.Department of Cilnical Laboratory,Chongqing Wanzhou Central Blood Station,Chongqing 404000,China
Abstract：Objective Design and synthesis of 4-nitro-1-naphthyl-β-D-galactopyranoside.Methods D-galactose reacted with sodium acetate and was obtained after esterification β-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(1H-NMR,13C-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-Dgalactopyranoside.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.
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