呋喃阿洛糖衍生物水解产物的结构确定

doi:10.11938/cjmr20170207

波谱学杂志 ›› 2017, Vol. 34 ›› Issue (2): 183-190.doi: 10.11938/cjmr20170207

呋喃阿洛糖衍生物水解产物的结构确定

张恩, 崔得运, 孙伟, 李鹏云, 徐锦梅, 刘宏民

郑州大学药学院, 河南郑州 450001

收稿日期:2016-03-03 修回日期:2017-04-18 出版日期:2017-06-05 发布日期:2017-06-05
通讯作者: 张恩Tel:18737134034,E-mail:zhangen@zzu.edu.cn;刘宏民,Tel:0371-67781739,E-mail:liuhm@zzu.edu.cn. E-mail:zhangen@zzu.edu.cn;liuhm@zzu.edu.cn
基金资助:
国家自然科学基金资助项目（81172937, U1204206）.

Structural Elucidation of a Hydrolysis Product from Derivatives of Allofuranose

ZHANG En, CUI De-yun, SUN Wei, LI Peng-yun, XU Jin-mei, LIU Hong-min

School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001, China

Received:2016-03-03 Revised:2017-04-18 Online:2017-06-05 Published:2017-06-05

摘要/Abstract

摘要： 1,2;5,6-双-O-异丙叉基-3-C-硝甲基-α-D-呋喃阿洛糖（化合物1）在酸性条件下选择性脱除5,6-异丙叉基得到C-3位构型保持的水解产物1,2-O-异丙叉基-3-C-硝甲基-α-D-呋喃阿洛糖（化合物2）；化合物1先经过Moffatt脱水生成C-3硝基烯产物1,2;5,6-双-O-异丙叉基-3-脱氧-亚甲基硝基-α-D-呋喃木糖（化合物3），然后在酸性条件下选择性脱除5,6-异丙叉基过程中协同发生氧杂-Michael加成反应得到C-3位构型反转的水解产物1,2-O-异丙叉基-3-C-硝甲基-α-D-呋喃葡萄糖（化合物2′），两种产物化合物2和2′互为C-3差向异构体.通过¹H NMR、¹³C NMR、DEPT-135、¹H-¹H COSY、gHSQC和gHMBC等核磁共振（NMR）技术，对化合物2′的¹H和¹³C NMR数据进行了全归属．

关键词: 归属, 水解产物, 核磁共振(NMR), 2D NMR

Abstract: 1,2-O-(1-methylethylidene)-3-C-methylnitro-α-D-allofuranose (2) was obtained through selective deprotection of 1,2;5,6-Di-O-isproplidene-3-C-methylnitro-α-D-allofuranose (1) under an acidic condition. C-3 nitrostyrenes (3) was synthetized through Moffatt dehydration from compound 1 under an acidic condition. A hydrolysis product 1,2-O-(1-methylethylidene)-3-C-methylnitro-α-D-glocufuranose (2') which had a reversed C-3 configuration was obtained by an unexpected oxa Michael addition. Compounds 2 and 2' were C-3 diasteroisomers. Compound 2' was characterized with NMR spectroscopy techniques, including ¹H NMR, ¹³C NMR, DEPT-135, ¹H-¹H COSY, gHSQC and gHMBC. ¹H and ¹³C chemical shifts of compound 2' were also fully assigned. The molecular structure of compound 2' was determined.

Key words: nuclear magnetic resonance (NMR), assignment, 2D NMR, hydrolysis product

中图分类号:

张恩, 崔得运, 孙伟, 李鹏云, 徐锦梅, 刘宏民. 呋喃阿洛糖衍生物水解产物的结构确定[J]. 波谱学杂志, 2017, 34(2): 183-190.

ZHANG En, CUI De-yun, SUN Wei, LI Peng-yun, XU Jin-mei, LIU Hong-min. Structural Elucidation of a Hydrolysis Product from Derivatives of Allofuranose[J]. Chinese Journal of Magnetic Resonance, 2017, 34(2): 183-190.

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呋喃阿洛糖衍生物水解产物的结构确定

Structural Elucidation of a Hydrolysis Product from Derivatives of Allofuranose

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