Synthesis of nucleoside thiophosphoanhydrides

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 29, 514 52, C07H 19067

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047287306

ABSTRACT:
A method for preparing sulfur and/or selenium containing phosphoanhydrides that have at least a triphosphate moiety is disclosed, together with a cyclo-intermediate formed during the reaction. The method includes reacting a first compound having an available and reactive group selected from phosphorodihalidate, thiophosphorodihalidate, and selenic phosphorodihalidate (the compound having a remaining portion that does not interfere with the reaction), with a second compound having an available and reactive group selected from phosphate, thiophosphate, and selenic phosphate (the second compound also having a remaining segment that does not interfere with the reaction). The selection of the reactive groups is such that at least one of the reactive groups is the thio or selenic variant, and the selection of the remaining portion and segment are such that at least one is attached to a linking group selected from phosphate, thiophosphate, and selenic phosphate that links it to the available and reactive group. The reaction appears to be best suited for creating nucleoside thiotriphosphates.

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