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4-Toluenesulfonyloxymethyl-(H)-phosphinate: A Reagent for the Introduction of O- and S-Methyl-(H)-phosphinate Moieties
- 1.0461797 - ÚOCHB 2017 RIV US eng J - Journal Article
Kostov, Ondřej - Páv, Ondřej - Buděšínský, Miloš - Liboska, Radek - Šimák, Ondřej - Petrová, Magdalena - Novák, Pavel - Rosenberg, Ivan
4-Toluenesulfonyloxymethyl-(H)-phosphinate: A Reagent for the Introduction of O- and S-Methyl-(H)-phosphinate Moieties.
Organic Letters. Roč. 18, č. 11 (2016), s. 2704-2707. ISSN 1523-7060. E-ISSN 1523-7052
R&D Projects: GA ČR GA13-26526S; GA MZd NV15-31604A; GA TA ČR TA03010598; GA MŠMT(CZ) LO1304
Institutional support: RVO:61388963
Keywords : acyclic nucleoside phosphonates * phosphinyl dipeptide isosteres * efficient synthesis
Subject RIV: CC - Organic Chemistry
Impact factor: 6.579, year: 2016
The straightforward synthesis of sodium 4-toluenesulfonyloxymethyl-(H)-phosphinate and (H)-phosphinomethylisothiouronium tosylate as new reagents for the preparation of O- and S-methyl-(H)-phosphinic acid derivatives, respectively, is described. The reactivity of both reagents was demonstrated by the preparation of protected 2'-deoxyribonucleoside-O-methyl-(H)-phosphinates in the 5'- and 3'-series and 2',5'-dideoxyribonudeoside-5'-S-methyl-(H)-phosphinates. These compounds represent a new class of monomers compatible with the solid phase synthesis of oligonucleotides by H-phosphonate chemistry, as it was proved with the synthesis of a fully phosphonate heptamer.
Permanent Link: http://hdl.handle.net/11104/0261379
Number of the records: 1