2-C-甲基-α-D-呋喃核糖四苯甲酸酯的合成

Synthesis of 1,2,3,5-tetra-O-benzoyl-2-C-methyl-βD-ribonfuranose

摘要:

以D-果糖为原料，经过内酯化反应、酰化、羰基还原、再次酰化4步反应合成2-C-甲基-α-D-呋喃核糖四苯甲酸酯（化合物 d），总收率为10.60%。采用1H-NMR、13C-NMR和MS等方法对中间产物和目标产物进行了结构表征。在2-C-甲基-D-核糖酸-1,4-内酯（a）的合成中，结合反应条件确定了最佳原料为D-果糖和氧化钙；通过对还原剂剂硼氢化钠﹑四氢化铝锂和红铝的比较，得出红铝为中间体2,3,5-三苯甲酰氧基-2-C-甲基-βD-呋喃核糖（c）合成的较优还原剂，还原收率可达96.20%；通过单因素考察确定三乙胺作为酰化反应的缚酸剂，酰化收率可达75.84%。

Abstract:

The 1,2,3,5-tetra-O-benzoyl-2-C-methyl-βD-ribonfuranose was synthesized from D-fructose by four steps, which were lactonization, acylation, reduction, and acylation, the overall yield was 10.6%. The characterization methods of 1HNMR、13C-NMR and MS were applied to confirm the structures of intermediates and product. Combining with the reduction condition, the best raw material for synthesizing 2-C-Methyl-D-ribonic-γ-lactone were D-fructose and CaO. The conclusion that the best reductant for 2,3,5-Tri-O-benzoyl-2-C-methyl-βD-ribofuranose is Red-Al was obtained by comparing using three different reductant as LiAlH4, NaBH4 and Red-Al and the yield can up to 96.20%.Through single factor experiments determented that triethylamine was the best acid binding agent for acylation reaction and the yield can up to 75.84%.