6-O-乙酰基-2，3，4-三-O-异丁酰基-β-D-吡喃葡萄糖的合成及应用

Synthesis of 6-O-Acetyl-2,3,4-tri-O-isobutyryl-β-D-glucopyranose and its Application in Cigarette

以β-D-甲基吡喃葡萄糖苷为起始原料,选择性地合成6-O-三苯甲基-β-D-甲基吡喃葡萄糖苷,再经异丁酰化和去三苯甲基保护基反应得到2,3,4-三-O-异丁酸-β-D-甲基吡喃葡萄糖苷酯,然后乙酯化生成6-O-乙酰基-2,3,4-三-O-异丁酰基-β-D-甲基吡喃葡萄糖苷,最后经无水HBr乙酸溶液处理后水解得到目标产物6-O-乙酰基-2,3,4-三-O-异丁酰基-β-D-吡喃葡萄糖(Ⅴ)。利用IR和1H NMR对每一步合成的产物结构进行了表征,并对添加和未添加Ⅴ的卷烟进行了主流烟气中异丁酸含量的GC/MS分析和评吸。结果表明:①Ⅴ为目标产物;②燃吸过程中Ⅴ裂解向烟气中释放26.10μg/mg异丁酸;③Ⅴ具有使卷烟烟气柔和,减少刺激性、杂气,改善余味,增强协调性的作用。

6 - O - trityl - β - D - methylglucopyranoside （ Ⅱ ） was selectively synthesized fromβ - D - methyl glueopyranoside （ Ⅰ ）, and then isobutyrylated, followed by detritylation to obtain 2, 3, 4 - tri - O - isobutyryl -β - D - methylglucopyranoside （ Ⅲ ） , which was subsequently acetylated to obtain 6 - O - acetyl - 2, 3, 4 - tri - 0 - isobutyryl -β - D - methylglucopyranoside （ Ⅳ ）. Finally, 6 - O - acetyl - 2, 3, 4 - tri - O - isobutyryl -β- D - glucopyranose （ V ） was prepared from the hydrolysis of Ⅳ at the presence of dry hydrogen bromide in glacial acetic acid. The products of all reaction steps were characterized with IR and 1H NMR. The cigarette applied with V was panel tested and the isobutyric acid in mainstream cigarette smoke was analyzed by GC/MS. The results showed that ： 1 ） the synthesized compound V was the target product ; 2） the isobutyric acid in cigarette smoke increased by 26.10 μg per milligram of Ⅴ added; 3） cigarette smoke was milder and more harmonious, had less offensive odor and irritation, and better aftertaste by Ⅴ application.