Journal article
Synthesis of nucleoside 3'-alkylphosphonates : intermediates for assembly of carbon-bridged dinucleotide analogues
Journal of organic chemistry, Vol.58(27), pp.7808-7812
1993
DOI: 10.1021/jo00079a027
Abstract
Several 3′-modified nucleosides have been prepared, through an initial Wittig or Horner-Wadsworth-Emmons condensation with an adenosine 3′-ketone, followed by catalytic hydrogenation of the resulting olefin. Subsequent reaction of the 3′α-methylene carboxylate with the lithium salt of diethyl ethylphosphonate gave a β-keto phosphonate, while reaction of the methylene carboxylate with LDA, diethyl chlorophosphite, and O2 gives the corresponding α-phosphono ester. These new nucleoside phosphonates can be viewed as analogues of natural phosphates and also can serve as synthetic intermediates for preparation of carbon-bridged dinucleotide analogues. To give the first such example, the β-keto phosphonate 13 was allowed to react with a nucleoside 5′-aldehyde, affording the dinucleoside enone 23. © 1993, American Chemical Society. All rights reserved.
Details
- Title: Subtitle
- Synthesis of nucleoside 3'-alkylphosphonates : intermediates for assembly of carbon-bridged dinucleotide analogues
- Creators
- KOO Lee - Univ. Iowa, dep. chemistry, Iowa City IA 52242, United StatesD. F Wiemer - Univ. Iowa, dep. chemistry, Iowa City IA 52242, United States
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.58(27), pp.7808-7812
- Publisher
- American Chemical Society
- DOI
- 10.1021/jo00079a027
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 1993
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9984216707302771
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