An Efficient Approach for the Synthesis of 1′-O-α-Methyl Pyrrolo[2,3-d]pyrimidine Isonucleosides

被引：5

作者：

Song, Yang ^{[1
]}

Yang, Ruchun ^{[2
]}

Ding, Haixin ^{[2
]}

Sun, Qi ^{[2
]}

Xiao, Qiang ^{[2
]}

Ju, Yong ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China

[2] Jiangxi Sci & Technol Normal Univ, Jiangxi Key Lab Organ Chem, Nanchang 330013, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2011年 / 08期

关键词：

pyrrolo[2,3-d]pyrimidine; isonucleoside; regioselective deprotection; triflate; cesium carbonate; PHASE-TRANSFER GLYCOSYLATION; ADENOSINE KINASE INHIBITORS; ANTIVIRAL ACTIVITY; ISOMERIC NUCLEOSIDES; ANALOGS; RIBONUCLEOSIDES; DEBENZYLATION; DERIVATIVES; LIQUID;

D O I：

10.1055/s-0030-1259961

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of novel 1'-O-alpha-methyl isonucleosides were efficiently and stereoselectively synthesized with 1,2,3,5-tetra-O-acetyl-D-ribofuranose as the starting material. The key steps include regioselective and stereoselective deprotection of the 2,4-dichlorobenzyl group at C2, triflation, and substitution with appropriate nucleobases using cesium carbonate as the base. Removal of the residual 2,4-dichlorobenzyl groups and subsequent transformation afforded the title compounds in 30-37% overall yield. The products represent a new type of isonucleosides with 1'-O-substitution.

引用

页码：1213 / 1218

页数：6

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