Methyl 4-toluenesulfonyloxymethylphosphonate, a new and versatile reagent for the convenient synthesis of phosphonate-containing compounds |
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| Authors: | Ivana K&#x;iov Zden k To
ík Milo&#x; Bud &#x;ínský Ond&#x;ej &#x;imk Radek Liboska Dominik Rejman Ond&#x;ej Pa
es Ivan Rosenberg |
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| Institution: | aInstitute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic v. v. i., Flemingovo 2, 16610 Prague 6, Czech Republic |
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| Abstract: | A straightforward procedure leading to the new phosphonylating reagent, methyl 4-toluenesulfonyloxymethylphosphonate, requiring no chromatographic purification is described. This stable reagent works with the same efficiency as dimethyl and other dialkyl esters for the introduction of an O-phosphonomethyl moiety while, in contrast to dimethyl ester, it does not cause any unwanted methylation of sensitive functionalities. Its utility for the alkylation of protected nucleosides in high yield is exemplified. |
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