Selective sulfonylation of 4-C-hydroxymethyl-β-L-threo-pento-1,4-furanose:: synthesis of bicyclic diazasugars

被引：28

作者：

Dhavale, DD ^{[1
]}

Matin, MM ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2004年 / 60卷 / 19期

关键词：

azasugars; bicyclic heterocyclic compounds; carbohydrates; enzyme inhibitors;

D O I：

10.1016/j.tet.2004.03.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydroxymethylation of alpha-D-xylo-pentodialdose 6 using excess formaldehyde and sodium hydroxide in THF-water (one pot aldol and crossed Cannizzaro reactions) followed by hydrogenolysis of C3-O-benzyl group afforded triol 8. The regio-selective alpha- and beta-sulfonylation of hydroxymethyl groups in 8 afforded 9a (alpha-sulfonylation) and 14 (beta-sulfonylation) in good yield. The cleavage of the 1,2-acetonide functionality, individually in 9a and 14, followed by reaction with 1,3-diaminopropane gave in situ formation of sugar aminals, that undergo concomitant nucleophilic displacement of the sulfonyloxy group by amino functionality to give hitherto unknown bicyclic diazasugars 4 and 5, respectively, with a hydroxymethyl substituent at C-7. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4275 / 4281

页数：7

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