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Nucleoside-O-Methyl-(H)-Phosphinates: Novel Monomers for the Synthesis of Methylphosphonate Oligonucleotides Using

Ondřej Kostov¹, Ondřej Páv¹, Ivan Rosenberg¹

¹Department of Bioorganic and Medicinal Chemistry, Institute of Organic Chemistry and Biochemistry of the CAS, Prague, Czech Republic.

Current Protocols in Nucleic Acid Chemistry

|September 19, 2017

Abstract:

This unit comprises the straightforward synthesis of protected 2'-deoxyribonucleoside-O-methyl-(H)-phosphinates in both 3'- and 5'-series. These compounds represent a new class of monomers compatible with the solid-phase synthesis of oligonucleotides using H-phosphonate chemistry and are suitable for the preparation of both 3'- and 5'-O-methylphosphonate oligonucleotides. The synthesis of 4-toluenesulfonyloxymethyl-(H)-phosphinic acid as a new reagent for the preparation of O-methyl-(H)-phosphinic acid derivatives is described. © 2017 by John Wiley & Sons, Inc.

Keywords:

H-phosphonate chemistry RNase H methylphosphonate modified oligonucleotide nucleoside-(H)-phosphinates

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