Alternative synthesis of cyclic IDP-carbocyclic ribose. Efficient cyclization of an 8-bromo-N1-[5-(phosphoryl)carbocyclic-ribosyl]inosine 5'- phenylthiophosphate derivative mediated by iodine

Article abstract of DOI:10.1016/S0040-4039(99)00977-6

An efficient synthesis of cyclic IDP-carbocyclic-ribose, as a stable mimic for cyclic ADP-ribose, was achieved. N¹-Carbocyclic-ribosylinosine derivative 15, prepared from N¹(2,4-dinitrophenyl)inosine derivative 10 and an optically active carbocyclic amine 11, was converted to 8-bromo-N¹- carbocyclic-ribosylinosine bis-phosphate derivative 20. Treatment of 20 with I₂ in the presence of molecular sieves in pyridine gave the desired cyclic product 8 quantitatively, which was deprotected and reductively debrominated to give the target cyclic IDP-carbocyclic ribose (3).