SIMPLIFIED SYNTHESIS OF 2'-O-ALKYL RIBOPYRIMIDINES

被引：14

作者：

HODGE, RP ^{[1
]}

SINHA, ND ^{[1
]}

机构：

[1] PERSEPT BIOSYST INC,NUCLEIC ACIDS RES GRP,BEDFORD,MA 01730

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 17期

关键词：

D O I：

10.1016/0040-4039(95)00435-F

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct 2'-hydroxyl alkylation (R= methyl, ethyl, propyl, pentyl or allyl) of 5'-dimethoxytrityl-N-(t-butylphenoxyacetyl or benzoyl)-cytidine 1 was achieved by reaction in the presence of silver I oxide and a catalytic amount of pyridine with excess alkyl halide. AT 0 degrees C alkylation of the 2'-hydroxyl was found to be highly selective; less than 10% dl (2'3')-O-alkylated or 3'-O-alkylated side products were detected in most cases. Quantitative deamination of 2'-O-alkylated cytidines to 2'-O-alkylated uridines were performed by refluxing in 4M aq. LiOH solution. This method simplifies access to various 2'-O-alkylated ribopyrimidines using readily available starting materials in one or two steps.

引用

页码：2933 / 2936

页数：4

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