Reductive cleavage of the O–C(8) bond in 5′-O,8-cycloadenosines. Intramolecular protection of the 8-position and the 5′-hydroxy group in adenosines

Abstract

Upon treatment with NaBH₃CN in acetic acid at ambient temperature, N⁶-acyl-5′-O,8-cycloadenosines (1) with or without carbon functional groups on the 2-position undergo exclusively a reductive O–C(8) bond cleavage to give the corresponding N⁶-acyladenosines (2).