Asymmetric dihydroxylation of D-glucose derived α,β-unsaturated ester:: Synthesis of azepane and nojirimycin analogues

被引：78

作者：

Dhavale, DD ^{[1
]}

Markad, SD

Karanjule, NS

PrakashaReddy, J

机构：

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

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 14期

关键词：

D O I：

10.1021/jo049509t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric dihydroxylation of a D-glucose derived a,P-unsaturated ester 3 afforded syn vicinal diols in good to high diastereoselectivity. The conversion of these vicinal diols to the corresponding cyclic sulfate, regio-, stereoselective nucleophilic ring opening by sodium azide, and LAH reduction afforded amino heptitols 7a,b that were converted to azepane 1c,d and nojirimycin analogues 2c,d.

引用

页码：4760 / 4766

页数：7

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