Novel and Efficient Synthesis of gem-Difluorinated Derivatives of Acyclic Nucleoside Phosphonates (ANPs)

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F16%3A00469886" target="_blank" >RIV/61388963:_____/16:00469886 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/slct.201600445" target="_blank" >http://dx.doi.org/10.1002/slct.201600445</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/slct.201600445" target="_blank" >10.1002/slct.201600445</a>

Result language
angličtina
Original language name
Novel and Efficient Synthesis of gem-Difluorinated Derivatives of Acyclic Nucleoside Phosphonates (ANPs)
Original language description
A novel efficient method for the synthesis of gem-difluorinated derivatives of acyclic nucleotide analogues has been developed. The method is based on utilization of diethyl difluoromethylphosphonate as a nucleophilic difluoromethylation reagent. In contrast to previous difluoromethylation procedures using commercially available DAST or deoxofluor, this process is very robust, proceeds under mild conditions and is accompanied only by small amounts of by-products. The reaction of diethyl difluoromethylphosphonate with 2-benzyloxyacetaldehyde afforded 3-(benzyloxy)-1,1-difluoropropan-2-ol (6) a key precursor for syntheses of difluoromethylated analogues of various acyclic nucleoside phosphonates.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/GA14-00522S" target="_blank" >GA14-00522S: Syntheses of new prodrug forms of biologically active nucleotide analogues</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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