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4-Toluenesulfonyloxymethyl-(H)-phosphinate: A Reagent for the Introduction of O- and S-Methyl-(H)-phosphinate Moieties. 2016
Ondřej Kostov, and
Ondřej Páv, and
Miloš Buděšínský, and
Radek Liboska, and
Ondřej Šimák, and
Magdalena Petrová, and
Pavel Novák, and
Ivan Rosenberg
Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
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'-dideoxyribonucleoside-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.
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