Synthesis of dinucleoside (N3′→MeP5′) methanephosphonamidates

Article abstract of DOI:10.1021/ol0259084

Three different approaches were used for the synthesis of dinucleoside methanephosphonamidates [3′-NH-P(O)(CH₃)O-5′], starting from dichloromethylphosphine or dichloromethanephosphonate as the phosphorus-containing moiety. 5′-DMT-3′-amino-3′-deoxythymidine and N(4)-benzoyl-5′-DMT-3′-amino-2′,3′-dideoxycytidine were used as the aminonucleoside precursors and the respective 3′-protected nucleosides (thymidine or N(4)-benzoyl-2′-deoxycytidine) as the 5′-hydroxyl reagents.