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An efficient synthesis of cyclic IDP-carbocyclic-ribose, as a stable mimic for cyclic ADP-ribose, was achieved. N 1 -Carbocyclic-ribosylinosine derivative 15, prepared from N 1 -(2,4-dinitrophenyl)inosine derivative 10 and an optically active carbocyclic amine 11, was converted to 8-bromo-N 1 -carbocyclic-ribosylinosine bis-phosphate derivative 20. Treatment of 20 with I ...
Formation of symmetric 36-membered-ring product 14 was observed in the synthetic study of a stable mimic of cyclic ADP-ribose (cADPR, 1). When 8-bromo-N 1 -[5-(phenylthiophosphoryl)carbocyclic-ribosyl]inosine 5'-phosphate derivative 5 was treated with AgNO 3 and Et 3 N in N-methyl-2-pyrrolidinone-HMPA (3:1), the substrate was dimerized and cyclized to give 14 in 39% yield.
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