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

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。

Abstract: Methyl-6-O-TBDPS-α-D-glucopyranoside (2) was selectively synthesized from methyl-α-D-glucopyranoside with high yield, and then isovalerylated, followed by deprotection, acetylation of 6-site and α-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.