Stereoselective synthesis of the C-4 linked imidazole nucleosides using modified Mitsunobu reaction

A highly stereoselective synthesis of the novel 4-(β-D-ribofuranosyl)imidazole 5 was accomplished in 4 steps and 85% overall yield from protected D-ribose 1. Cyclization of the diol (RS)- 3 having an intact imidazole by modified Mitsunobu reaction exclusively afforded benzylated β-ribofuranosylimida...

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Bibliographic Details
Published inTetrahedron letters Vol. 36; no. 18; pp. 3165 - 3168
Main Authors Harusawa, Shinya, Murai, Yoshihiko, Moriyama, Hideki, Ohishi, Hirofumi, Yoneda, Ryuji, Kurihara, Takushi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.05.1995
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
C-NUCLEOSIDES
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Summary:A highly stereoselective synthesis of the novel 4-(β-D-ribofuranosyl)imidazole 5 was accomplished in 4 steps and 85% overall yield from protected D-ribose 1. Cyclization of the diol (RS)- 3 having an intact imidazole by modified Mitsunobu reaction exclusively afforded benzylated β-ribofuranosylimidazole β- 4a, accompanied by α- 4a, in a ratio of 26:1. Reductive debenzylation completed the synthesis. 2′-Deoxy derivative 8 was also synthesized stereoselectively in the same manner. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)00503-5