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
收藏
页码：941 / 946
页数：6
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