3-甲基丁醇基-β-D-吡喃葡萄糖苷的合成及表征
毕业论文关键词: 3-甲基丁醇基-β-D-吡喃葡萄糖苷；潜香物质；合成；表征
Synthesis and Characterization of 3-methyl-1-butyl-β-D- glucopyranoside Abstract: The flavor precursors play a crucial role in regulating cigarette aroma because thay can gradually release the durable, uniform, full of rich aroma in the pyrolysis process and have good thermal stability. In this paper, we used anhydrous D-glucose as a starting material, reacting with acetic anhydride to form 1,2,3,4,6-penta-O-acetyl-β-D-glucose via esterification. Via Helferich Synthesis 1,2,3,4,6-penta-O-acetyl-β-D-glucose was transferred 3-methyl-1-butyl-2,3,4,6-tetraacetyl-β-D-glucopyranoside, which was hydrolyzed in the presence of sodium methoxide to afford the target compound 3-methyl-1-butyl-β-D-glucopyranoside. The synthetic process of glycosides was optimized and the optimal conditions were: Catalyst dosage: ether solution of boron trifluoride: 1,2,3,4,6-penta-acetyl -O-β-D-glucose=1:4, molar ratio of reactants: 3-methyl-1-butanol: 1,2,3,4,6-penta-acetyl -β-D-O-glucose 2:1, temperature 25 ℃, time 2.5 hours. All intermediates and the targetproduct were characterized by H-NMR and MS. Finally, the target product was added into cigarette and an artificial smoking evaluation was carried out.
Key words: 3-methyl-1-butyl-β-D-glucopyranoside; flavor precursors; synthesis; characterization
目录
1综述 1
1.1 引言 . 1
1.2糖类化合物介绍 1
1.2.1 单糖（monosaccharides）及单糖衍生物 1
1.2.2 低聚糖（oligosaccharides，寡糖） 2
1.2.3 多糖（polysaccharides） 3
1.3 糖类化合物的合成方法 . 3
1.3.1 Koenigs-Knorr 合成法 4
1.3.2 Helferich 反应 . 5
1.3.3 Fischer糖苷化法 6
1.3.4 三氯乙酰亚氨酸酯法 6
1.3.5 硫代糖苷法 7
1.3.6 三卤代乙酸酯法 7
1.4 糖苷类潜香物质 . 8
1.4.1 糖苷的存在形式 8
1.4.2 糖苷类潜香物质的研究进展 8
1.4.3 存在问题 9
1.5本论文的研究目的和意义 10
1.5.1 研究目的 10
1.5.2 研究意义 10
1.6设计路线 11
2 实验内容 12
2.1原料及仪器 12
2.1.1 所需原料 12
2.1.2 所需仪器 12
2.2化合物的合成路线 13
2.2.1 1,2,3,4,6-五-O-乙酰基-β-D-葡萄糖的合成 . 13
2.2.2 3-甲基丁基-2,3,4,6-四乙酰基-β-D-吡喃葡糖的合成 14
2.2.3 3-甲基丁醇基-β-D吡喃葡萄糖苷的合成 . 14
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