Stereoselective Synthesis of Quercetin 3-O-Glycosides of 2-Amino-2-Deoxy-d-Glucose Under Phase Transfer Catalytic Conditions

被引：12

作者：

Cao, Zhiling ^{[1
]}

Qu, Yingying ^{[1
]}

Zhou, Jiexing ^{[1
]}

Liu, Weiwei ^{[1
]}

Yao, Guowei ^{[2
]}

机构：

[1] Huaihai Inst Technol, Sch Chem Engn, Jiangsu Key Lab Marine Biotechnol, Lianyungang 222005, Peoples R China

[2] Beijing Inst Technol, Sch Life Sci, Beijing 100081, Peoples R China

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2015年 / 34卷 / 01期

关键词：

Phase transfer catalysis; 2-Amino-2-deoxy-d-glucose; Quercetin; Stereoselective synthesis; Glycosides; DIETARY SOURCES; GLYCOSYLATION; FLAVONOIDS; GLYCOPEPTIDES; GLUCOSAMINE; METABOLITES; PREVENTION; GLYCOSIDES; ANALOGS; RUTIN;

D O I：

10.1080/07328303.2014.996290

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

This article describes the stereoselective synthesis of quercetin 3-O-glycosides of 2-amino-2-deoxy-d-glucose. Efficient 1,2-trans-glycosylation of protected quercetin with N-acetyl-protected 2-amino-2-deoxy-d-glucose chloride was achieved under phase transfer catalytic conditions in a 0.15M aqueous K2CO3/chloroform system using tetrabutylammonium bromide as the catalyst. On the contrary, glycosylation with the N-phthalimido-protected bromide donor under the same conditions was found to give predominantly 1,2-cis-glycoside product.

引用

页码：28 / 40

页数：13

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