7-羟基香豆素基α-L-阿拉伯呋喃糖苷的合成  

Synthesis of Umbelliferyl-α-L-Arabinofuranoside

作　　者：罗春[1] 徐黔江[1] 

机构地区：[1]贵阳医学院药学院,贵州贵阳550004

出　　处：《化学试剂》2015年第10期945-947,960,共4页Chemical Reagents

摘　　要：以L-阿拉伯糖为原料,经3步反应得到全乙酰化阿拉伯糖。随后,以全乙酰化阿拉伯糖为原料,合成了各种糖基供体。最后将这些糖基供体和7-羟基香豆素进行糖苷化反应条件优化,经过一系列的条件筛选,最后发现,以全乙酰化-L-阿拉伯糖为糖基供体、120 mol%的Sn Cl4为活化剂、乙腈为溶剂,在-10℃下加入反应,最后缓慢升温至室温反应24 h。在这一条件下,以70%的收率得到标题化合物。随后,在碱性条件下水解乙酰基,以83%的收率得到标题化合物。Started from L-arabinose,1,2,3,5-tetra-O-acetyl-L-arabinose was synthesized via 3 steps reaction. With peracetylatedL-arabinose,some other glycosyl donors were prepared,and used to screen the glycosylation conditions with 7-hydroxycoumarin. It was found that the peracetylated-L-arabinose offered the desired glycosylation in highest yield（ 70%） with 120 mol%. of Sn Cl4 as promoter and CH3 CN as solvent. The obtained umbelliferyl 2,3,5-tri-O-acetyl-α-L-Arabinofuranoside was further deacetylation with TEA in methanol achieved umbelliferyl α-L-Arabinofuranoside in 83% yield.

关 键 词：呋喃糖苷 阿拉伯糖 7-羟基香豆素 SNCL4 

分 类 号：O629.13[理学—有机化学]