New short route to unsaturated fluoroketonucleosides: Case of 5-fluoro-1-(6-O-acetyl-3,4-di-deoxy-3-fluoro-beta-D-glycero-hex-3-eno-pyranos-2-ulosyl) uracil

The proposed short synthesis involves two key steps: Oxidation of the isopropylidene derivative of the 3 fluoronucleoside possessing a free hydroxyl group in 2-position and acetylation of deprotected 3-fluoro-2-ketonucleoside which, after a beta-elimination reaction, gives the desired unsaturated ke...

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Published inNucleosides, nucleotides & nucleic acids Vol. 24; no. 4; pp. 243 - 246
Main Authors Egron, MJ, Komiotis, D, Dorange, Herscovici, J, Ollapally, AP, Antonakis, K
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 01.01.2005
Subjects
Biochemistry & Molecular Biology
Chromatography, Thin Layer
Fluorine - chemistry
Fluorouracil - analogs & derivatives
Fluorouracil - chemical synthesis
Fluorouracil - pharmacology
Immunosuppressive Agents - pharmacology
Ketones - chemistry
Life Sciences & Biomedicine
Magnetic Resonance Spectroscopy
Models, Chemical
Nucleosides - chemical synthesis
Nucleosides - chemistry
Science & Technology
Uracil - analogs & derivatives
Uracil - chemical synthesis
AGENT
DERIVATIVES
BIOLOGICAL-ACTIVITY
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Summary:The proposed short synthesis involves two key steps: Oxidation of the isopropylidene derivative of the 3 fluoronucleoside possessing a free hydroxyl group in 2-position and acetylation of deprotected 3-fluoro-2-ketonucleoside which, after a beta-elimination reaction, gives the desired unsaturated ketonucleoside 5.
Bibliography:Medline
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1525-7770
1532-2335
DOI:10.1081/NCN-200059683