title: 4-Toluenesulfonyloxymethyl-(H)-phosphinate: A Reagent for the Introduction of O- and S-Methyl-(H)-phosphinate Moieties.
abstract: 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.
authors.affiliation: Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.|Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Prague , Technická 5, 160 00 Prague 6, Czech Republic.
authors.forename: Ondřej
authors.initials: O
authors.lastname: Kostov
authors.affiliation: Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
authors.forename: Ondřej
authors.initials: O
authors.lastname: Páv
authors.affiliation: Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
authors.forename: Miloš
authors.initials: M
authors.lastname: Buděšínský
authors.affiliation: Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
authors.forename: Radek
authors.initials: R
authors.lastname: Liboska
authors.affiliation: Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.|Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Prague , Technická 5, 160 00 Prague 6, Czech Republic.
authors.forename: Ondřej
authors.initials: O
authors.lastname: Šimák
authors.affiliation: Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
authors.forename: Magdalena
authors.initials: M
authors.lastname: Petrová
authors.affiliation: Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
authors.forename: Pavel
authors.initials: P
authors.lastname: Novák
authors.affiliation: Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
authors.forename: Ivan
authors.initials: I
authors.lastname: Rosenberg