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An examination of amines as catalysts for the first-step phosphorylation of nucleosides by a two-step phosphorylating agent, 2-methylthio-4H-1,3,2-benzodioxaphosphorin 2-oxide (MTBO, 2), revealed that, in the presence of 4-morpholine-N,N′-dicyclohexylcarboxamidine (MDC, 3) as the catalyst, MTBO phosphorylates and o-hydroxybenzylates adenosine borate complex (1) to give 1-(o-hydroxybenzyl)adenosine 5′-S-methyl phosphorothiolate (5), with subsequent Dimroth rearrangement to give N6-(o-hydroxybenzyl)adenosine 5′-S′-methyl phosphorothiolate (6).The guanosine borate complex (7) gave 1-(o-hydroxybenzyl)guanosine 5′-S-methyl phosphorothiolate (8) under the same conditions.MTBO phosphorylated N6-benzyladenosine and N6-allyladenosine borate complexes (9a and b) in the presence of n-propylamine (11) to give their 5′-S-methyl phosphorothiolates (10a and b), respectively.Thus, the 5′-S-methyl phosphorothiolates of cytokinin-like nucleosides were synthesized by the use of different amine catalysts from both intact and...

agricultural and biological chemistry

Specific Effects of 4-Morpholine-N,N'-dicyclohexylcarboxamidine as a Catalyst for the Alkylation and Phosphorylation of Ribonucleosides by a Two-step Phosphorylating Agent, MTBO: Its Application to the Synthesis of Cytokinin-like Nucleotides.