SYNTHESIS OF 5'-O-AMINO-2'-DEOXYPYRIMIDINE AND PURINE NUCLEOSIDES - BUILDING-BLOCKS FOR ANTISENSE OLIGONUCLEOSIDES

被引：26

作者：

PERBOST, M ^{[1
]}

HOSHIKO, T ^{[1
]}

MORVAN, F ^{[1
]}

SWAYZE, E ^{[1
]}

GRIFFEY, RH ^{[1
]}

SANGHVI, YS ^{[1
]}

机构：

[1] ISIS PHARMACEUT,DEPT MED CHEM,CARLSBAD,CA 92008

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 16期

关键词：

D O I：

10.1021/jo00121a037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of 5'-O-amino-2'-deoxy analogs of uridine 1, thymidine 2, cytidine 3, 5-methylcytidine 3a, adenosine 4, and guanosine 5 was accomplished. The key step of 5'-O-N-bond formation in 2'-deoxynucleosides 1-5 was achieved via a Mitsunobu reaction in excellent yields. The 5'-O-amino nucleosides 1-5 are useful building-blocks for the synthesis of nucleoside dimers linked by a methylene(methylimino) (MMI) bridge. MMI is a novel phosphate surrogate for antisense oligonucleosides.

引用

页码：5150 / 5156

页数：7

共 53 条

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