葡萄糖3,5-二硝基苯甲酸酯在合成葡萄糖苷和相关寡糖中的应用

葡萄糖3,5-二硝基苯甲酸酯在合成葡萄糖苷和相关寡糖中的应用

黄河清, 李清, 蔡孟深, 李中军^*

1.北京大学药学院化学生物学系, 北京 100083;
2.新乡医学院化学系, 河南新乡 453003

收稿日期:2004-06-10 修回日期:2004-11-10 出版日期:2004-12-15 发布日期:2004-12-15
通讯作者: 李中军*

Use of Glucosyl 3,5-Dinitrobenzoate in Synthesis of Glucosides and Related Oligosaccharides

HUANG He-qing, LI Qing, CAI Meng-shen, LI Zhong-jun^*

1.Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China;
2.Department of Chemistry, Xinxiang Medical College, Xinxiang 453003, China

Received:2004-06-10 Revised:2004-11-10 Online:2004-12-15 Published:2004-12-15
Contact: LI Zhong-jun*

摘要/Abstract

摘要： 目的探索一种新型的糖基化方法. 方法以TMSOTf为催化剂, 1-α-O-(3, 5-二硝基苯甲酰基)-2, 3, 4, 6-四-O-苄基-D-吡喃葡萄糖分别与一系列的羧酸、酚、醇和单糖反应, 得到糖基化产物, 采用¹H、¹³C NMR谱确证了产物的构型. 结果高立体选择性、较好收率地得到了α-葡萄糖苷和相应的寡糖. 结论 3,5-二硝基苯甲酰氧基作为良好的糖端基离去基用于寡糖的合成, 具有反应条件温和、收率较高、立体选择性好的特点.

关键词: 葡萄糖基3,5二硝基苯甲酸酯, 葡萄糖基3,5二硝基苯甲酸酯, 葡萄糖基3,5二硝基苯甲酸酯, 糖基化反应, 糖基化反应, 糖基化反应, 立体选择性, 立体选择性, 立体选择性

Abstract: Aim To investigate a new glycosylation method. Methods In the presence of TMSOTf as catalyst, 1-O-(3, 5-dinitrobenzoyl)-2, 3, 4, 6-tetra-O-benzyl-α-D-glucopyranose 1 reacted with a series of carboxylic acid, phenols, alcohols and saccharides respectively to give the corresponding glycosylation products. The compounds were determined by ¹H NMR and ¹³C NMR spectra. Results The α-gluco-pyranosides and related oligosaccharides were prepared in high yields. Conclusion The 3, 5-dinitrobenzoyl group was found to be a good leaving group at the anomeric position and O-glucopyranosides and oligosaccharides were stereoselectively synthesized in good yield.

Key words: glucosyl 3,5-dinitrobenzoate, glucosyl 3,5-dinitrobenzoate, glycosylation, glycosylation, stereoselectivity, stereoselectivity

中图分类号:

R916.41

Supporting: Foundation item: National Natural Science Foundation of China (20372003, 30330690).
^*Corresponding author. Tel.: 86-10-82801504

黄河清, 李清, 蔡孟深, 李中军^*. 葡萄糖3,5-二硝基苯甲酸酯在合成葡萄糖苷和相关寡糖中的应用[J]. .

HUANG He-qing, LI Qing, CAI Meng-shen, LI Zhong-jun^*. Use of Glucosyl 3,5-Dinitrobenzoate in Synthesis of Glucosides and Related Oligosaccharides[J]. .

[1]	天然药物及仿生药物国家重点实验室. 叶新山团队在立体选择性电糖基化方面取得进展[J]. 中国药学(英文版), 2020, 29(9): 671-672.
[2]	冯金, 梁文飞, 季帅, 乔雪, 张英涛, 余四旺, 叶敏. Isoangustone A的冻土毛霉生物转化研究[J]. 中国药学(英文版), 2015, 24(5): 285-291.
[3]	孙晟, 马庆, 孟祥豹, 李庆, 李树春, 黄河清, 李中军^*. 离子液体在甘露糖苷化过程中的β导向性: 一种具有选择性构建1,2-顺式-β-D-甘露糖连接潜力的新方法[J]. , 2011, 20(6): 549-556.
[4]	刘会臣, 杨燕燕, 刘铁军, 侯艳宁. 正常人体内反式曲马多活性代谢物O-去甲基曲马多对映体的药代动力学[J]. , 2000, 9(3): 151-154.