摘要就以往文献及研究中报道的收率不高或者后处理比较繁琐的问题，在通过阅 读查阅文献后，本课题拟改变以往的苄基糖的合成过程，合成在糖苷表面活性剂 及药物中间体领域具有很高应用价值的2,3,4,6-O-四苄基-α-D-葡萄糖，并对各种反 应条件进行选择探索从而获得最佳的反应条件，并提高收率。68428

本文中由D-葡萄糖起始，通过1-甲氧基葡萄糖合成、2,3,4,6-四苄基-1-甲氧基 葡萄糖合成等中间反应最终生成2,3,4,6-O-四苄基-D-葡萄糖。又进一步与N-酰基丙 氨酸反应，生成2,3,4,6,-O-四苄基-D-葡萄糖酯衍生物。对于产物运用了核磁、质谱 和红外光谱等方法监测分析。

毕业论文关键词：D-葡萄糖；1-甲氧基葡萄糖；苄基保护；合成

Title    Synthesis of2,3,4,6-O-tetrabenzyl-D-glucose

Abstract

Reported in the literature and research on past yield is not high or relatively tedious post-processing problems,through reading.After reading literature,this study intends to change the past,benzyl sugar synthesis, synthetic surfactant in glycoside and2,3,4,6-O-Four benzyl- α-D-glucose with high drug intermediate value of the field,and to explore the various reaction conditions are selected to obtain the optimum reaction conditions,and improve yield.

The starting article from D-glucose,by a 1-methoxy synthesis of glucose,2.3.4.6-four benzyl-1-methoxy-glucose synthesis reaction of the resulting intermediate 2,3,4,6-O-four benzyl-D-glucose.Further reacted with an N-acyl alanine,generated2,3,4,6-O-four benzyl-D-alkanyl glucose.For product use of NMR,mass spectrometry and infrared spectroscopy methods for monitoring analysis.

Key word: D-glucose;1-methoxy-glucose;benzyl protecting;Synthesis

目录

1 绪论 1

1.1 概述 1

1.1.1 表面活性剂 1

1.1.2 糖类表面活性剂 1

1.1.3 羟基的保护 2

1.2 苄基保护的应用 4

1.2.1 苄基保护的α-D-葡萄糖三氯乙酰亚胺酯 4

1.2.2 2,3,4,6-O-四苄基葡萄糖三氯乙酰亚胺酯 5

1.2.3 八苄基蔗糖及其水解反应 6

1.3 本课题的研究目的及意义 7

1.4 本课题的研究内容 7

2 2,3,4,6-O-四苄基-D-葡萄糖的合成 8

2.1 实验部分 8

2.1.1 主要试剂与溶剂 8

2.1.2 仪器设备 9

2.2 1-甲氧基葡萄糖的制备 9

2.2.1 合成路线 9