Volume 31, Issue 12
Natural Products
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ChemInform Abstract: Facile Synthesis and Conformation of 3′-O,4′-C-Methyleneribonucleosides.

Satoshi Obika

Satoshi Obika

Grad. Sch. Pharm. Sci., Osaka Univ., Suita, Osaka 565, Japan

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Ken-ichiro Morio

Ken-ichiro Morio

Grad. Sch. Pharm. Sci., Osaka Univ., Suita, Osaka 565, Japan

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Yoshiyuki Hari

Yoshiyuki Hari

Grad. Sch. Pharm. Sci., Osaka Univ., Suita, Osaka 565, Japan

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Takeshi Imanishi

Takeshi Imanishi

Grad. Sch. Pharm. Sci., Osaka Univ., Suita, Osaka 565, Japan

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First published: 09 June 2010

Abstract

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ChemInform Abstract

A novel and practical route to the title compounds (XII) (4 examples) involving the coupling of 1-O-acetylribofuranose derivatives [cf. (VII)] with silylated nucleobase [→(IX)] and a subsequent oxetane ring formation [→(XI)] as the key steps is developed. NMR and X-ray analysis indicates that the ribofuranose ring of nucleoside analogue (XII) is found to exist predominantly in a S-conformation.

chemical structure image

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