Synthesis of an uncharged cAMP-analogue

Article abstract of DOI:10.1080/15257779508014657

3'-O,5'-N-(N-phenylsulfonyliminocarbonyl)-5'-amino-5'-deoxy adenosine, an uncharged cAMP-analogue was synthesized. This was accomplished by treatment of 5'amino-5'-deoxy-2',3'-O-isopropylidene adenosine with dimethyl N-phenylsulfonyldithiocarbamate. After removal of the isopropylidene protecting group and treatment of the intermediate with benzoyl chloride, cyclisation was carried out in DMF containing 10 equivalents of potassium tert-butoxide. Final deprotection of the adenine moiety was carried out with hydrazine hydrate.