Synthesis of carbocyclic pyrimidine nucleosides, III.: Influence of the N3-protection group on N1-vs. O2-alkylation in the Mitsunobu reaction

被引：32

作者：

Ludek, OR ^{[1
]}

Meier, C ^{[1
]}

机构：

[1] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 04期

关键词：

carbocyclic nucleosides; regioselectivity; nucleoside analogues; antiviral agents; Mitsunobu reaction;

D O I：

10.1002/ejoc.200500801

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The influence of the N3-protection group of thymine on the regioselectivity of the N1- vs. O-2-alkylation under Mitsunobu conditions is described. A series of N3-protected thymine derivatives 8a-f was prepared and coupled to cyclopentanol as model compound for carbocyclic nucleoside precursors. Finally, the N3-BOM group was selected to improve our previously reported synthetic strategy to carbocyclic thymidine (carba-dT). Moreover, the 2,6-dimethyl-Bz group led exclusively to the O-2-analogue of carba-dT. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006.

引用

页码：941 / 946

页数：6

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