DIVERGENT AND STEREOCONTROLLED APPROACH TO THE SYNTHESIS OF URACIL NUCLEOSIDES BRANCHED AT THE ANOMERIC POSITION

被引：54

作者：

ITOH, Y ^{[1
]}

HARAGUCHI, K ^{[1
]}

TANAKA, H ^{[1
]}

GEN, E ^{[1
]}

MIYASAKA, T ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 03期

关键词：

D O I：

10.1021/jo00108a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrophilic addition of NBS/pivalic acid (bromopivaloyloxylation) to 1-[3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-D-erythro-pent- 1-enofuranosyl]uracil (2), readily accessible from O-2,2'-anhydro-uridine, furnished 1-[2-bromo-3,5-bis-O-(tert-butyldimethyylsilyl)-2-deoxy-1-(pivaloyloxy)-beta-D-ara-binofuranosyl]uracil (7) stereoselectively. This compound (7), having a leaving group at the 1'-position as well as 2'-beta-Br that could exert anchimeric assistance, serves as versatile intermediate for the stereocontrolled synthesis of various types of 1'-C-branched derivatives through nucleophilic substitutions by the use of organosilicon and organoaluminum reagents. The whole sequence constitutes the first example of the conversion of a naturally-occurring nucleoside to the analogues branched at the anomeric position.

引用

页码：656 / 662

页数：7

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