大学化学 >> 2016, Vol. 31 >> Issue (4): 60-66.doi: 10.3866/PKU.DXHX20160460

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甲基2, 3, 4, 6-四-O-苯甲酰基-α-D-吡喃甘露糖苷的合成及结构表征——推荐一个综合药物合成实验

刘美艳,曾佑林*()   

  • 发布日期:2016-05-06
  • 通讯作者: 曾佑林 E-mail:youlinzengcn@gmail.com
  • 基金资助:
    国家自然科学基金面上项目(21272064);湖南省教育厅资助科研项目(12C0249);湖南师范大学实习基地项目(043-008)

Synthesis and Structural Characterization of Methyl 2, 3, 4, 6-tetra-Obenzoyl-α-D-mannopyrannoside

Mei-Yan LIU,You-Lin ZENG*()   

  • Published:2016-05-06
  • Contact: You-Lin ZENG E-mail:youlinzengcn@gmail.com
  • Supported by:
    国家自然科学基金面上项目(21272064);湖南省教育厅资助科研项目(12C0249);湖南师范大学实习基地项目(043-008)

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摘要：

介绍一个综合药物合成实验——甲基2, 3, 4, 6-四-O-苯甲酰基-α-D-吡喃甘露糖苷的合成及结构表征。以D-甘露糖为原料,经费歇尔糖苷化和苯甲酰化合成甲基2, 3, 4, 6-四-O-苯甲酰基-α-D-吡喃甘露糖苷。用薄层色谱监测反应进程,采用过滤、洗涤、浓缩、萃取、干燥、柱层析等操作对中间体和目标产物进行分离纯化,并通过熔点和旋光度测定、核磁共振、红外光谱对其结构进行表征。

关键词: 反应进程监测, D-甘露糖结构表征, 药物合成实验

Abstract:

A new comprehensive drug synthesis experiment was introduced in this article. From commercially available D-mannose, methyl 2, 3, 4, 6-tetra-O-benzoyl-α-D-mannopyrannoside was synthesized via Fischer-Helferich glycosylation followed by benzoylation. The intermediate and the target compound were purified by filtration, washing, concentration, extraction, drying, and silicon column separation. The structure was characterized by the infrared spectrum (IR), nuclear magnetic resonance (NMR) spectrum, measurements of melt point and optical rotation of the compound.

Key words: Reactionmonitoring, D-mannose, Structural characterization, Drug synthesis experiment