Efficient Synthesis of 7,4'-Dimethylapigenin-5-O-glycoside

doi:10.6023/cjoc201807041

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (2): 561-565.DOI: 10.6023/cjoc201807041 Previous Articles Next Articles

Notes

7,4'-二甲氧基洋芹素-5-O-葡萄糖苷的高效合成

颜世强, 李英霞

复旦大学药学院上海 201203

收稿日期:2018-07-23 修回日期:2018-08-25 发布日期:2018-09-10
通讯作者: 李英霞 E-mail:liyx417@fudan.edu.cn
基金资助:
国家自然科学基金（No.81773576）资助项目.

Efficient Synthesis of 7,4'-Dimethylapigenin-5-O-glycoside

Yan Shiqiang, Li Yingxia

School of Pharmacy, Fudan University, Shanghai 201203

Received:2018-07-23 Revised:2018-08-25 Published:2018-09-10
Contact: 10.6023/cjoc201807041 E-mail:liyx417@fudan.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 81773576).

1. Efficient Synthesis of 7,4'-Dimethylapigenin-5-O-glycoside.PDF(412KB)

Abstract

As the active component of precious Chinese medicine Aquilaria sinensis, 7,4'-dimethylapigenin-5-O-glycoside showed inhibitory activity for nitric oxide (NO) production by activated RAW 264.7 cells. Because of the strong intramolecular H-bond, the 5-O-glucosidic linkage in flavonoids could not be efficiently constructed via conventional glycosylation method. In this paper, the efficient chemical synthesis of 7,4'-dimethylapigenin-5-O-glycoside has been achieved for the first time starting from commercially available naringenin and D-glucose via a linear reaction sequence of 6 steps with the overall yield of 36.0%, wherein selective hydroxy protecting, reduction with sodium borohydride, glycosylation under phase transfer catalytic condition, oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and other reactions were used. This work definitely laid the foundation for the further pharmacological study of this natural compound.

Key words: Aquilaria sinensis, 7,4'-dimethylapigenin-5-O-glycoside, flavonoids, chemical synthesis

Cite this article

Yan Shiqiang, Li Yingxia. Efficient Synthesis of 7,4'-Dimethylapigenin-5-O-glycoside[J]. Chin. J. Org. Chem., 2019, 39(2): 561-565.

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7,4'-二甲氧基洋芹素-5-O-葡萄糖苷的高效合成

Efficient Synthesis of 7,4'-Dimethylapigenin-5-O-glycoside

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