Synthesis of dinucleoside phosphates and their analogs by the boranophosphotriester method using azido-based protecting groups

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Oligodeoxyribonucleotides and their backbone-modified analogs were synthesized in good yields by the boranophosphotriester method in solution. The oligodeoxyriobonucleoside boranophosphates, fully protected with 2-(azidomethyl)benzoyl groups, were converted to the various backbone-modified DNA analogs via the corresponding H-phosphonate intermediates. A new efficient protecting group for the O 6-position of 2′-deoxyguanosine, 4-[(2-azidomethyl)benzoyloxy]benzyl (AZBn) group, was also developed. The AZBn group was found to be quickly removed by treatment with MePPh 2 in dioxane–2-mercaptoethanol–H 2O.