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Novel and Efficient Synthesis of gem-Difluorinated Derivatives of Acyclic Nucleoside Phosphonates (ANPs)
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SYSNO ASEP 0469886 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Novel and Efficient Synthesis of gem-Difluorinated Derivatives of Acyclic Nucleoside Phosphonates (ANPs) Author(s) Pomeisl, Karel (UOCHB-X) RID
Beier, Petr (UOCHB-X) RID, ORCID
Pohl, Radek (UOCHB-X) RID, ORCID
Krečmerová, Marcela (UOCHB-X) RID, ORCIDSource Title ChemistrySelect. - : Wiley - ISSN 2365-6549
Roč. 1, č. 10 (2016), s. 2102-2106Number of pages 5 s. Language eng - English Country DE - Germany Keywords difluoromethylation ; difluoromethylphosphonate ; acyclic nucleoside phosphonate ; phosphonate ester ; microwave reaction Subject RIV CC - Organic Chemistry R&D Projects GA14-00522S GA ČR - Czech Science Foundation (CSF) Institutional support UOCHB-X - RVO:61388963 UT WOS 000395417800003 DOI 10.1002/slct.201600445 Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2017
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