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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

  • 摘要: 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1HNMR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。

     

    Abstract: 6-O-trityl-β-D-methylglucopyranoside(Ⅱ) was selectively synthesized from β-D-methylglucopyranoside(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-O-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 1HNMR.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.

     

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