Selective sulfonylation of 4-C-hydroxymethyl-β-L-threo-pento-1,4-furanose:: synthesis of bicyclic diazasugars
Selective sulfonylation of 4-C-hydroxymethyl-β-L-threo-pento-1,4-furanose:: synthesis of bicyclic diazasugars
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DOI：
10.1016/j.tet.2004.03.034
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发表时间：
2004-05-03
期刊：
影响因子：
2.1
通讯作者：
Matin, MM
中科院分区：
文献类型：
--
作者：
Dhavale, DD;Matin, MM
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.
