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1,2,3,5-四-O-苯甲酰基-2-C-甲基-β-D-呋喃核糖(化合物d),总收率为10.60%。采用1HNMR、13CNMR和MS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-β-D-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%。
1,2,3,5-Tetra-O-benzoyl-2-C-methyl-fl-D-ribofuranose was synthesized from D-fructose by a four-step reaction of lactonization, acylation, reduction and acylation, and the overall yield was 10. 60%. The characterization methods of 1HNMR,13 CNMR and MS were applied to confirm the structures of the intermediates and the final product. Judging from the reaction conditions, the best raw materials for synthesizing 2-C-methyl-D-ribonic-y-lactone were D-fructose and CaO. The conclusion that the best reductant for 2,3,5-tri-O-benzoyl-2-C-methyl-fl-D-ribofuranose is Red-A1 was obtained by comparing the three different reductants of LiA1H4, NaBH4 and Red-A1. With this reductant, the yield can be up to 96.20%. Through single factor experiments it was determined that triethylamine was the best acid binding agent for acylation reaction and the yield can be up to 75.84%.
出处
《精细化工》
EI
CAS
CSCD
北大核心
2013年第11期1290-1293,共4页
Fine Chemicals
