Aziridine carboxylate from D-glucose: synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition

被引：38

作者：

Dhavale, DD ^{[1
]}

Kumar, KSA

Chaudhari, VD

Sharma, T

Sabharwal, SG

PrakashaReddy, J

机构：

[1] Univ Poona, Dept Chem, Garware Res Ctr, Pune 411007, Maharashtra, India

[2] Univ Poona, Dept Chem, Div Biochem, Pune 411007, Maharashtra, India

[3] Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 20期

关键词：

D O I：

10.1039/b509216g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The D-glucose derived aziridine carboxylate 5 was obtained from (E)-ethyl-6-bromo-1,2-O-isopropylidene-3-O-benzyl-5-deoxy-alpha-D-xylo-5-eno-heptofuranuronate 4 through conjugate addition of benzylamine and in situ intramolecular nucleophilic expulsion of bromine. The regioselective aziridine ring-opening, using water as a nucleophile, resulted in the alpha-hydroxy-beta-aminoester 6, which was exploited in the synthesis of six and five membered azasugars 1b/1c and 2b/2c, respectively The glycosidase inhibitory activity of the title compounds was evaluated.

引用

页码：3720 / 3726

页数：7

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