An efficient synthetic approach to all of four 2'-C-a-aminomethyl-2'-deoxynucleosides (15 ; U, C, A, G) from methyl 3,5-di-O-benzyl-2-keto-a-D-ribofuranoside (1 ) is developed. The synthesis is achieved efficiently via the convergent approach involving glycosylation of persilylated nucleobases with 2-a-phthalimidomethyl ribofuranoside 3 . Optimal conditions for subsequent debenzylation depended on the nucleobase. For guanosine derivatives, debenzylation by Pd or Pd(OH)2 catalyzed hydrogenation gives product in better yield. For uridine, cytidine and adenosine derivatives, boron trichloride induced benzyl ether cleavage gives products in higher yield.

Synthesis of 2'-C-α-aminomethyl-2'-deoxynucleosides

243rd National Meeting (2012)

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