FACILE SYNTHESES OF PSEUDO-ALPHA-D-ARABINOFURANOSE, AND 2 PSEUDO-D-ARABINOFURANOSYLNUCLEOSIDES, (+)-CYCLARADINE AND (+)-1-PSEUDO-BETA-D-ARABINOFURANOSYLURACIL, FROM D-ARABINOSE

被引：28

作者：

YOSHIKAWA, M ^{[1
]}

YOKOKAWA, Y ^{[1
]}

INOUE, Y ^{[1
]}

YAMAGUCHI, S ^{[1
]}

MURAKAMI, N ^{[1
]}

KITAGAWA, I ^{[1
]}

机构：

[1] OSAKA UNIV,FAC PHARMACEUT SCI,SUITA,OSAKA 565,JAPAN

来源：

TETRAHEDRON | 1994年 / 50卷 / 33期

关键词：

D O I：

10.1016/S0040-4020(01)89611-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An optically active pseudo-sugar, pseudo-alpha-D-arabinofuranose, was efficiently synthesized from D-arabinose by using a stereoselective nitromethane addition reaction to form a branched nitropyranose (6) as a key step. Furthermore, two biologically active pseudo-beta-D-arabinofuranosylnucleosides, (+)-cyclaradine and (+)-1-pseudo-beta-D-arabinofuranosyluracil, were also synthesized from the nitrocyclopentene derivative (12), which was prepared from a synthetic intermediate of pseudo-arabinofuranose, via Michael-type reaction introducing nucleic acid base moieties.

引用

页码：9961 / 9974

页数：14

共 27 条

[1] SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].