Uridine 5'-monoselenoacetals as substrates for diastereoselective homolytic C-C bond formation

被引：8

作者：

Haraguchi, K ^{[1
]}

Tanaka, H ^{[1
]}

Saito, S ^{[1
]}

Kinoshima, S ^{[1
]}

Hosoe, M ^{[1
]}

Kanmuri, K ^{[1
]}

Yamaguchi, K ^{[1
]}

Miyasaka, T ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1996年 / 52卷 / 28期

关键词：

monoselenoacetal; uridine; radical reaction; C-C bond formation; diastereoselectivity;

D O I：

10.1016/0040-4020(96)00483-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Uridine 5'-monoselenoacetals prepared by the seleno-Pummerer reaction of 5 '-deoxy-5'-phenylseleno-uridines were used ar substrates for radical-mediated reactions with allyltributyltin. The reaction of the 2'3'-O-iso-propylidene derivative gave cyclized product, 5-allyl-6,5'-cyclonucleosides, whereas those of the 2',3'-bis-O-(tert-butyldimethylsilyl derivatives underwent the C-C bond formation at the 5'-position to give (S'S)- and (S'R)-isomers. The stereochemical outcome of both types of reactions is discussed. The use of radical accepters other than allyltributyltin was also examined. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：9469 / 9484

页数：16

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