[N:1]([C:4](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([P:18]([O:24][O:25][CH2:26][CH3:27])([O:20][O:21][CH2:22][CH3:23])=[O:19])[OH:17])=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[N+]=[N-].[H][H]>CO.[Pd]>[CH2:22]([O:21][O:20][P:18]([CH:16]([OH:17])[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH:4]([C:5]([O:7][CH3:8])=[O:6])[NH2:1])=[CH:11][CH:12]=1)([O:24][O:25][CH2:26][CH3:27])=[O:19])[CH3:23]A total of 3.4 g (9.2 mmol) of 38 in 100 mL MeOH was hydrogenated at 40 psi H2 over 300 mg 10% Pd.C. Hydrogen was replenished at t=15, 60, 135, 210 and 255 minutes and 300 mg additional 10% Pd, C was added at t=135 and 255 minutes and the reaction terminated at t=6 hours. The mixture was filtered through celite and rotovapped (30° C.) to yield 39 as a clear colorless oil (2.97 g, 95%). The oil crystallized from ether yielding white crystals, mp 94°-100° C. (soften 77° C.). 1H NMR (250 MHz, DMSO-d6) δ: 7.34 (d, 2H, J=7.5 Hz, aromatic), 7.15 (d, 2H, J=7.5 Hz, aromatic), 6.16 (br s, 1H, OH) , 4.89 (d,1H, J=13.0 Hz, PCH), 3.93 (m, 4H, OCH2), 3.59 (m, 1H, Hα), 3.57 (s, 3H, CO2CH3), 2.87 (dd, 1H, J=13.4, 6.7 Hz, Hβ), 2.76 (dd, 1H, J=13.4, 7.2 Hz, Hβ) , 1.17 (t, 3H, J=7.0 Hz, CH3), 1.13 (t, 3H, J=7.0 Hz, CH3), mp 94°-100° C.; FABMS m/z 346.1 (M+H)+.
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