HCID 86600751, compound → HCID 11215979, compound
Reaction equation
C([O:8][C@@H:9]1[C@@H:16]([O:17]CC2C=CC=CC=2)[C@H:15]([O:25]CC2C=CC=CC=2)[C@@H:14]([CH2:33][O:34][C:35]2[CH:36]=[C:37]([C:41]3[CH:46]=[CH:45][C:44]([C@@H:47]4[C@@H:50]([CH2:51][CH2:52][C@@H:53]([C:55]5[CH:60]=[CH:59][C:58]([F:61])=[CH:57][CH:56]=5)[OH:54])[C:49](=[O:62])[N:48]4[C:63]4[CH:68]=[CH:67][C:66]([F:69])=[CH:65][CH:64]=4)=[CH:43][CH:42]=3)[CH:38]=[CH:39][CH:40]=2)[O:13][C@@H:10]1[O:11][CH3:12])C1C=CC=CC=1>C(O)C.[Pd]>[F:69][C:66]1[CH:67]=[CH:68][C:63]([N:48]2[C:49](=[O:62])[C@H:50]([CH2:51][CH2:52][C@@H:53]([C:55]3[CH:56]=[CH:57][C:58]([F:61])=[CH:59][CH:60]=3)[OH:54])[C@H:47]2[C:44]2[CH:43]=[CH:42][C:41]([C:37]3[CH:38]=[CH:39][CH:40]=[C:35]([O:34][CH2:33][C@H:14]4[O:13][C@H:10]([O:11][CH3:12])[C@H:9]([OH:8])[C@@H:16]([OH:17])[C@@H:15]4[OH:25])[CH:36]=3)=[CH:46][CH:45]=2)=[CH:64][CH:65]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Methyl 2,3,4-tri-O-benzyl-6-O-(4′-{(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}biphenyl-3-yl)-α-D-glucopyranoside (70 mg, 0.08 mmol) was dissolved in absolute ethanol (3 mL). 10% Pd/C (wet, 14% w/w) was added and the vessel sealed. The solution was degassed by evacuation and flushing with hydrogen gas at balloon pressure. The reaction was monitored by TLC (1:1 hexane-ethyl acetate). Upon completion, the catalyst was filtered by passing through a plug of Celite® and washing with additional ethanol. The filtrate was concentrated in vacuo and purified by preparative HPLC (Polaris C18-A 10 μ 250×21.2 mm column, 30% to 95% acetonitrile-0.1% trifluoroacetic acid in water) affording methyl 6-O-(4′-{(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}biphenyl-3-yl)-α-D-glucopyranoside (18.1 mg, 36% yield); 1H NMR (300 MHz, CDCl3/1% CD3OD) δ 7.58 (d, J=8.4 Hz, 2H), 7.38-7.23 (m, 7H), 7.17-7.14 (m, 2H), 7.04-6.92 (m, 5H), 4.80 (d, J=3.9 Hz, 1H), 4.70 (d, J=2.4 Hz, 1H), 4.67 (t, J=5.7 Hz, 1H), 4.37-4.33 (m, 1H), 4.26-4.21 (m, 1H), 3.92-3.87 (m, 1H), 3.74-3.45 (m, 3H), 3.42 (s, 3H), 3.18-3.10 (m, 1H), 2.01-1.88 (m, 4H) ppm; MS [M−OH]+ 644.0.