Investigation of a facile synthetic method for phosphorothioate dimer synthons in oligonucleotide phosphorothioates synthesis.
A facile synthetic method of a phosphorothioate dimer block was investigated. Dinucleoside phosphite triester intermediates were obtained in one-pot synthesis by the coupling of a protected nucleoside bearing free 5'-OH and a protected nucleoside bearing free 3'-OH in the presence of phosphorous trichloride (PCl3) and 1,2,4-triazole. The intermediates were easily sulfurized to afford the desired phosphorothioate dimer blocks in 33-64% overall yields.
Miyashita
T
T
Chemistry Lab., Yamasa Corporation, Chiba, Japan. miyasita@yamasa.com
Yamada
K
K
Kondo
K
K
Mori
K
K
Shinozuka
K
K
D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis*; D013464:Sulfuric Acids / Q000737:chemistry; D013873:Thionucleotides / Q000138:chemical synthesis*; D014230:Triazoles / Q000737:chemistry
D009841:Oligonucleotides; D013464:Sulfuric Acids; D013873:Thionucleotides; D014230:Triazoles