Chiral Vinylphosphonate and PhosphonateAnalogues of the Immunosuppressive AgentFTY720

摘要

The first enantioselective synthesis of chiral isosteric phos-phonate analogues of FTY720 is described. One of theseanalogues, FTY720-(E)-vinylphosphonate (S)-5, but not its Renantiomer, elicited a potent antiapoptotic effect in intestinalepithelial cells, suggesting that it exerts its action via theenantioselective activation of a receptor. (S)-5 failed to activatethe sphingosine 1-phosphate type 1 (S1P_1) receptor.