STEREOSELECTIVE SYNTHESIS OF THE C-4 LINKED IMIDAZOLE NUCLEOSIDES USING MODIFIED MITSUNOBU REACTION

被引：27

作者：

HARUSAWA, S ^{[1
]}

MURAI, Y ^{[1
]}

MORIYAMA, H ^{[1
]}

OHISHI, H ^{[1
]}

YONEDA, R ^{[1
]}

KURIHARA, T ^{[1
]}

机构：

[1] OSAKA UNIV PHARMACEUT SCI,MATSUBARA,OSAKA 580,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 18期

关键词：

D O I：

10.1016/0040-4039(95)00503-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective synthesis of the novel 4-(beta-D-ribofuranosyl)imidazole 5 was accomplished in 4 steps and 85% overall yield from protected D-ribose 1. Cyclization of the diet (RS)-3 having an intact imidazole by modified Mitsunobu reaction exclusively afforded benzylated beta-ribofuranosylimidazole beta-4a, accompanied by alpha-4a, in a ratio of 26:1. Reductive debenzylation completed the synthesis. 2'-Deoxy derivative 8 was also synthesized stereoselectively in the same manner.

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页码：3165 / 3168

页数：4

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