6-O-乙酰基-2,3,4-三-O-异戊酰基-α-D-吡喃葡萄糖的合成及热裂解  

Synthesis and Pyrolysis of 6-O-Acetyl-2,3,4-tri-O-Isovaleryl-α-D-Glucopyranose

作　　者：郑赛晶[1] 薄飞[2] 方嵩[2] 刘百战[1] 李有桂[2] 

机构地区：[1]上海烟草集团有限责任公司技术中心,上海市长阳路717号200082 [2]合肥工业大学化学工程学院,合肥市屯溪路193号230009

出　　处：《烟草科技》2012年第11期51-55,共5页Tobacco Science & Technology

基　　金：上海烟草集团有限责任公司卷烟烟气烟草行业重点实验室开放课题"蔗糖四元酯的合成及在卷烟中的应用"(CF56.1-ZJ3)

摘　　要：以α-D-甲基吡喃葡萄糖苷为原料,高产率、选择性地合成了6-O-叔丁基二苯基硅基-α-D-甲基吡喃葡萄糖苷(2),再经异戊酰化、脱TBDPS保护基、6-位乙酰化及α-位甲氧基乙酰化,然后再用乙酸肼处理得到目标产物6-O-乙酰基-2,3,4-三-O-异戊酰基-α-D-吡喃葡萄糖(1)。用1H NMR和HRMS谱对糖酯1的结构进行了表征。结果表明:①合成产物(1)为目标产物糖酯;②燃吸过程中糖酯1热裂解可向烟气中释放38.7μg/mg的异戊酸。Methyl-6-O-TBDPS-α-D-glucopyranoside （2） was selectively synthesized from methyl-a-D-glucopyra- noside with high yield, and then isovalerylated, followed by deprotection, acetylation of 6-site and a-site methoxyl group to form Compound 6. 6-O-Acetyl-2, 3, 4-tri-O-isovaleryl-α-D-glucopyranose （1） was obtained from the hydrolysis of Compound 6 in the presence of hydrazine acetate. The target compound and intermediates were characterized by HRMS and 1H NMR spectra. The results showed that： synthetic Compound 1 was the target product; Compound 1 could release 38.7 μg/mg of isovaleric acid to cigarette smoke during smoking.

关 键 词：葡萄糖酯 异戊酸 卷烟烟气 裂解 

分 类 号：O621.3[理学—有机化学]