Journal article
Synthesis of 5'-amino-5'-phosphonate analogues of pyrimidine nucleoside monophosphates
Journal of organic chemistry, Vol.68(16), pp.6108-6114
08/08/2003
DOI: 10.1021/jo030050x
PMID: 12895038
Abstract
The 5'-amino-5'-phosphono derivatives of cytidine, cytosine arabinoside (ara-C), and uridine have been prepared via the corresponding nucleoside aldehydes. Phosphite addition to imines derived from the nucleoside aldehydes and p-methoxybenzylamine was efficient, and use of this amine allowed cleavage of the products to the parent amino phosphonic acids. The phosphite additions proved to be diastereoselective, with the cytidine and uridine derivatives favoring the 5'S stereochemistry and the ara-C derivative favoring the 5'R isomer. The stereochemistry of one cytidine derivative was established by single-crystal diffraction analysis, and detailed comparisons of the (13)C NMR data allowed assignments of the other amino phosphonates.
Details
- Title: Subtitle
- Synthesis of 5'-amino-5'-phosphonate analogues of pyrimidine nucleoside monophosphates
- Creators
- Xuemei Chen - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, USADavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.68(16), pp.6108-6114
- DOI
- 10.1021/jo030050x
- PMID
- 12895038
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- United States
- Language
- English
- Date published
- 08/08/2003
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9983985946402771
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