Nucleosides and nucleotides .138. Synthesis of 3-halo-3-deazainosines: Conformational lock with the halogen at the 3-position of the 3-deazainosine in anti-conformation

被引：7

作者：

Minakawa, N ^{[1
]}

Kojima, N ^{[1
]}

Matsuda, A ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,KITA KU,SAPPORO,HOKKAIDO 060,JAPAN

来源：

HETEROCYCLES | 1996年 / 42卷 / 01期

关键词：

D O I：

10.3987/COM-95-S57

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of 3-chloro-, bromo-, and iodo-3-deazainosines (6-8) can be done by treatment of the 3-deazainosine derivative (2) with N-halosuccinimides. Treatment of the 5-formylimidazole derivative (11) with vinylmagnesium bromide gave 5-(1-hydroxy-2-propenyl)imidazole derivative (12), followed by fluorination and appropriate manipulations to cyclize, affording 3-fluoro-3-deazainosine (18). Although free rotation around the glycosyl linkage in 3-deazainosine (1) and 18 was observed, those of 6, 7, and 8 were rather fixed in the anti-conformation as analyzed by nOe experiments.

引用

页码：149 / 154

页数：6

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