碳苷研究(Ⅰ)--取代芳基溴化镁与α-卤代-D-四-O-乙酰吡喃葡萄糖的反应

高等学校化学学报 ›› 1987, Vol. 8 ›› Issue (6): 511.

碳苷研究(Ⅰ)--取代芳基溴化镁与α-卤代-D-四-O-乙酰吡喃葡萄糖的反应

蔡孟深, 岳保珍, 王少农, 毛阿利, 邱东旭

北京医科大学药学院

收稿日期:1985-11-16 出版日期:1987-06-24 发布日期:1987-06-24
基金资助:
中国科学院科学基金

Studies on C-Glycosides(Ⅰ)--The Reaction Between Substituted Phenylmagnesium Bromides and α-D-Tetraacetyl-Glucopyranosyl Halide

Cai Mengshen, Yeu Baozhen, Wang Shaonong, Mao Ali, Qiu Dongxu

College of Pharmacy Beijing Medical University, Beijing

Received:1985-11-16 Online:1987-06-24 Published:1987-06-24

摘要/Abstract

摘要： 本文报道了取代芳基溴化镁与α-溴代-D-四-O-乙酰葡萄糖的反应。4-甲氧基取代时影响不大,收率较好且以β碳苷为主要产物。2-甲氧基取代时反应产物复杂,分离出四个产物,均已鉴定。2,4-二甲氧基取代时,也有四个产物,但只对其α-及β-碳苷进行了分离鉴定。2-苄氧基取代及2,6-二苄氧基取代时则因位阻较大,C₁^'位亲核取代反应难以发生。

Abstract: The reactions between substituted phenylmagnesium bromides and α-D-tetra-acetyl-glucopyranosyl halides were studied. 4-methoxy phenylmagnesium bromides gave mainly β-C-glucoside.In the case of 2-methoxy-phenylmagnesium bromide,four products were obtained. They were l-α-(2-methoxy phenyl)-2,3,4,6-D-tetraace-tyl glucopyranoside, 1-β-(2-methoxy phenyl)-D-triacetyl-glucopyranoside, D-tetra-acetylglucopyranose,and l-deoxy-2-(2-methoxy phenyl)-2,3,4,6-D-tetraacetylglu-copyranoside. 2, 4-dimethoxyphenylmagncsium bromide, both α-and β-C-glucosides were separated. In the cases of 2-benzyloxy and 2,6-dibenzyloxy phenylmagne-sium bromides, the steric effect of the bulky substituents at ortho position prevented normol coupling reaction.

TrendMD:

蔡孟深, 岳保珍, 王少农, 毛阿利, 邱东旭. 碳苷研究(Ⅰ)--取代芳基溴化镁与α-卤代-D-四-O-乙酰吡喃葡萄糖的反应. 高等学校化学学报, 1987, 8(6): 511.

Cai Mengshen, Yeu Baozhen, Wang Shaonong, Mao Ali, Qiu Dongxu . Studies on C-Glycosides(Ⅰ)--The Reaction Between Substituted Phenylmagnesium Bromides and α-D-Tetraacetyl-Glucopyranosyl Halide. Chem. J. Chinese Universities, 1987, 8(6): 511.