苯甲醇基-β-D-吡喃葡萄糖苷的合成及表征

摘要: 苯甲醇基-β-D-吡喃葡萄糖苷是应用于加香卷烟中的糖苷类潜香物质。本课题以D-葡萄糖作为原料，与乙酸酐酯化生成1,2,3,4,6-五-O-乙酰基-β-D-葡萄糖，再利用Helferich法合成苯甲醇基-2，3，4，6-四乙酰基-β-D-吡喃葡糖苷，然后通过水解反应，得到化合物苯甲醇基-β-D-吡喃葡萄糖苷。所得产物经核磁共振氢谱、MS 图谱进行结构表征后，确认产物与目标化合物结构一致。对Helferich法合成糖苷的实验条件进行归纳讨论，得到本实验的最优条件为：反应时间2.5h；反应温度25℃；1，2，3，4，6-五-O-乙酰基-β-D-葡萄糖和催化剂摩尔比4：1；苯甲醇和苯甲醇基-β-D-吡喃葡萄糖苷摩尔比2：1。产物的最终产率为18.4%。 56987
毕业论文关键词：葡萄糖苷；合成优化；潜香物质
Synthesis and Characterization of benzyl alcohol groups -β-D- glucopyranoside
Abstract: Benzene methanol based -β-D-glucopyranoside is glycosidic aroma precursors used in cigarette flavoring. Using D-glucose as the raw material of this topic, with acetic anhydride esterification 1,2,3,4,6-penta-O- acetyl -β-D- glucose, the use of Helferich method for the synthesis of benzyl alcohol based -2, 3, 4, 6- tetra-acetyl -β-D-glucopyranoside, then through hydrolysis reaction, compounds of benzene methanol based -β-D-glucopyranoside. After the structure was characterized by nuclear magnetic resonance spectroscopy and high performance liquid chromatography, the results confirmed that the product was consistent with the structure of the target compound. The experimental conditions for the synthesis of glycosides from the Helferich method are discussed and summarized, and a preliminary exploration for the optimization of the synthesis process is carried out. The optimal conditions are as follows: Reaction time 2.5h; Reaction temperature 25℃; The ratio of 1,2,3,4,6-penta-O- acetyl -β-D- glucose and catalyst molar 4:1; The ratio of alcohol and sugar molar: 2:1. The final yield rate of the product is18.4%.
Keywords: Glucoside; Synthesis; Latent fragrant substances

1 绪论 . 1

1.1 引言 . 1

1.2 糖苷类化合物的合成研究进展 . 1

1.2.1 Koenigs-knorr法 2

1.2.2 Fischer法 . 3

1.2.3 相转移催化法 4

1.3 糖苷类潜香物质概述 . 4

1.4 烟草中糖苷类潜香物质的种类 4

1.5 烟草中糖苷类潜香物质的分离与鉴定 5

1.6 烟草中糖苷类潜香物质的作用 . 6

1.7 烟草中糖苷类潜香物质的应用研究 . 6

1.8 研究方案 . 8

2 实验部分 . 9

2.1 实验试剂和仪器设备 9

2.1.1 实验试剂 9

2.1.2 实验设备 9

2.2 实验过程步骤 . 10

2.2.1 1，2，3，4，6-五-O-乙酰基-β-D-葡萄糖的合成 10

2.2.2 苯甲醇基-2，3，4，6-四乙酰基-β-D-吡喃葡糖苷的合成 . 10

2.2.3 成苷反应实验条件优化 . 11

2.2.4 苯甲醇基-β-D-吡喃葡糖苷的合成 . 14

3 实验结果与讨论 16

3.1 乙酰化反应 16

3.2 成苷反应 . 16

3.3 糖苷的水解反应 16

3.4 苯甲醇基-β-D-吡喃葡糖苷的结构鉴定 17

4 结论 19

致谢 20 苯甲醇基-β-D-吡喃葡萄糖苷的合成及表征:http://www.youerw.com/huaxue/lunwen_61572.html