NUCLEIC-ACID RELATED-COMPOUNDS .71. EFFICIENT GENERAL-SYNTHESIS OF PURINE (AMINO, AZIDO, AND TRIFLATE)-SUGAR NUCLEOSIDES

被引：58

作者：

ROBINS, MJ ^{[1
]}

HAWRELAK, SD ^{[1
]}

HERNANDEZ, AE ^{[1
]}

WNUK, SF ^{[1
]}

机构：

[1] UNIV ALBERTA,DEPT CHEM,EDMONTON T6G 2E1,ALBERTA,CANADA

来源：

NUCLEOSIDES & NUCLEOTIDES | 1992年 / 11卷 / 2-4期

关键词：

D O I：

10.1080/07328319208021743

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Treatment of 3',5'-O-(tetraisopropyldisiloxanyl)adenosine and its arabino epimer with trifluoromethanesulfonyl chloride/DMAP gave the 2'-triflates in high yields. Displacements (LiN3/DMF) and deprotection gave 2'-azido-2'-deoxyadenosine and its arabino epimer which were reduced with Bu3SnH/AIBN/DMAC/benzene (or Staudinger reduction) to give 2'-amino-2'-deoxyadenosine and its epimer. Oxidation of 2',5'-bis-O-(tert-butyldimethylsilyl)adenosine, stereoselective reduction, triflation, azide displacement, deprotection, and reduction gave 3'-amino-3'-deoxyadenosine.

引用

页码：821 / 834

页数：14

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