期刊
TETRAHEDRON
卷 65, 期 18, 页码 3673-3681出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.02.071
关键词
Tartaric acid; Pyrrolidine derivatives; Nucleoside analogues; Nucleotide analogues; Phosphonate; Nucleobase; Mannich; Michael
资金
- Ministry of Education, Youth andof the Czech Republic [2B06065]
- Ministry of Health of the Czech Republic [NR/9138-3]
- MEYS, CR [MSM0021620835]
- Research Centres [LC06077, LC06061]
- Acad. Sci., CR [KAN200520801]
- Institute research project [Z40550506]
N-Phosphonoalkyl-trans-3,4-dihydroxypyrrolidine derivatives were synthesized and exploited as synthons for the preparation of hydroxypyrrolidine nucleoside phosphonic acids, the 3'-deoxynucleoside 5'-phosphate analogues. Simultaneously, an alternative route, the N-phosphoalkylation of the preformed pyrrolidine nucleosides employing Mannich- and Michael-type reactions, was investigated to obtain desired nucleotide analogues. In contrast to the latter approach, the former resulted in the formation of two diastereoisomers very likely due to the existence of two possible S(N)2 transition states during a nucleophilic displacement. The stereochernistry of the prepared nucleotide analogues was studied by NMR spectroscopy. (C) 2009 Elsevier Ltd. All rights reserved.
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