M. Uchiyama

Nonaqueous oxidation of nucleoside phosphites to the phosphates

Abstract Bis (trimethylsilyl) peroxide, t -butyl hydroperoxide, cumene hydroperoxide, and N -methylmorpholine N -oxide serve as excellent agents for anhydrous oxidation of nucleoside phosphites to the phosphates. The reaction using bis (trimethylsilyl) peroxide is conspicuously accelerated by added trimethylsilyl triflate or Nafion-TMS.

Allyl protection of internucleotide linkage

Abstract Allyl group serves as a useful protecting group for an internucleotide bond, which can be removed mildly by brief treatment with a catalytic amount of Pd[P(C 6 H 5 ) 3 ] 4 and various nucleophiles.

A convenient method for the formation of internucleotide linkage

Abstract Internucleotide linkage can be made readily by reaction of N -unprotected nueleosides and phosphorochloridates or p -nitrophenyl phosphates by the assistance of Grignard reagents.

Facile nucleoside phoshorylation via hydroxyl activation

Abstract A rapid preparation of nucleoside phosphates under very mild conditionis is described.

Chemoselective phosphorylation of N-unprotected nucleosides via aluminum alkoxides

An O-selective phosphorylation of NH2-unprotected nucleosides has been achieved via the aluminum alkoxides.

Solid-phase synthesis of oligodeoxyribonucleotides using the bis(trimethylsilyl) peroxide oxidation of phosphites

Abstract The trimethylsilyl triflate-catalyzed bis(trimethylsilyl) peroxide oxidation of phosphites has been successfully applied to the solid-phase synthesis of d (AAGATC).

A convenient synthesis of 2−–5− linked oligoribonucleotides

Abstract A general synthesis of 2−–5− linked oligoribonucleotides has been achieved on the basis of chemoselective formation of the 2−–5− internucleotide linkage using N -unblocked nucleosides.

ELECTROCHEMICAL REMOVAL OF ALLYLIC PROTECTING GROUPS IN NUCLEOTIDE SYNTHESIS

Abstract Electrochemical, palladium(0)-mediated removal of allylic protecting groups of nucleosides and nucleotides is described. This method required no chromatographic treatment for isolation of the products. This paper is dedicated to the late Dr. Tsujiaki Hata in recognition of his outstanding contribution to nucleic acid science.