Efficient and versatile protocols for the synthesis of chiral analogues of the novel immunomodulator FTY720 and its phosphate are described. These synthetic procedures allow for broad structural variation and deliver essential tools to further elucidate FTY720's novel mechanism of action. OP), 6.86 (d, J = 8 Hz, 2 H arom ), 7.13 (d, J = 8 Hz, 2 H arom ). MS (ES+): m/z = 398.3 (MH) + , 795.3 (2 M + H) + . MS (ES-): m/z = 396.3 (M -H) -, 397.3 (M -), 793.3 (2M -H) -. (6) 1 H NMR (400 MHz, DMSO-d 6 ): d = 0.90 (t, J = 7 Hz, 3 H, CH 3 ), 1.25-1.53 [m, 10 H, CH 2 , (CH 2 ) 4 ], 1.65-1.85 (m, 6 H, 2 × C q -CH 2 , OCH 2 CH 2 ), 2.53 (m, 2 H, PhCH 2 ), 3.43 (m, 2 H, CH 2 OH), 3.88 (d, J = 7 Hz, 2 H, CH 2 OP), 3.94 (t, J = 7 Hz, 2 H, PhOCH 2 ), 6.86 (d, J = 8 Hz, 2 H arom ), 7.12 (d, J = 8 Hz, 2 H arom ).
Phosphoric Acid Mono-{(S)-2-amino-2-[2-(4-heptyloxyphenyl)ethyl]-5-hydroxypentyl} EsterMS (ES+): m/z = 418.3 (MH) + , 873.4 (2 M + K) + . MS (ES-): m/z = 416.4 (M -H) -, 417.3 (M -), 833.5 (2 M -H) -.