RADICAL-INITIATED 1,2-ACYLOXY MIGRATION WHICH GENERATES A NUCLEOSIDE ANOMERIC RADICAL

被引：26

作者：

ITOH, Y ^{[1
]}

HARAGUCHI, K ^{[1
]}

TANAKA, H ^{[1
]}

MATSUMOTO, K ^{[1
]}

NAKAMURA, KT ^{[1
]}

MIYASAKA, T ^{[1
]}

机构：

[1] SHOWA UNIV,SCH PHARMACEUT SCI,SHINAGAWA KU,TOKYO 142,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 22期

关键词：

RADICAL REACTION; URACIL NUCLEOSIDE; 12-ACYLOXY MIGRATION; ANOMERIC RADICAL; C-C BOND FORMATION;

D O I：

10.1016/0040-4039(95)00718-R

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Face-selectivity of bromo-pivaloyloxylation to 1'2'-unsaturated uridine can be altered by changing the 3'5'-O-protecting group. The resulting 2'-bromo-1'-pivaloyloxylated adduct, upon being reacted under radical conditions, undergoes 1,2-acyloxy migration to generate a nucleoside anomeric radical which was allowed to react with Bu(3)SnH or allyltributyltin. Factors governing stereochemistry and efficacy of this migration are also discussed.

引用

页码：3867 / 3870

页数：4

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