alpha-D-Glucopyranosyl bromide, tetraacetate → 3-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyloxy)-4-[(4-{2-[2-{[4-(benzyloxycarbonyl)piperazin-1-yl]carbonyl}-2-(methyl)propionylamino]ethoxy}-2-methylphenyl)methyl]-5-isopropyl-1H-pyrazole
Reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]([CH3:44])([CH3:43])[C:20]([NH:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][C:33]3[C:34](=[O:41])[NH:35][NH:36][C:37]=3[CH:38]([CH3:40])[CH3:39])=[C:28]([CH3:42])[CH:27]=2)=[O:21])=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:45][C:46]([O:48][CH2:49][C@H:50]1[O:55][C@H:54](Br)[C@H:53]([O:57][C:58]([CH3:60])=[O:59])[C@@H:52]([O:61][C:62]([CH3:64])=[O:63])[C@H:51]1[O:65][C:66]([CH3:68])=[O:67])=[O:47].CC(OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O)=O>>[C:58]([O:57][C@@H:53]1[C@@H:52]([O:61][C:62](=[O:63])[CH3:64])[C@@H:51]([O:65][C:66](=[O:67])[CH3:68])[C@@H:50]([CH2:49][O:48][C:46](=[O:47])[CH3:45])[O:55][C@H:54]1[O:41][C:34]1[C:33]([CH2:32][C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH2:23][NH:22][C:20](=[O:21])[C:19]([C:17]([N:14]3[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])[CH2:16][CH2:15]3)=[O:18])([CH3:44])[CH3:43])=[CH:27][C:28]=2[CH3:42])=[C:37]([CH:38]([CH3:39])[CH3:40])[NH:36][N:35]=1)(=[O:59])[CH3:60]Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared in a similar manner to that described in Reference Example 17 using 4-[(4-{2-[2-{[4-(benzyloxycarbonyl)piperazin-1-yl]carbonyl}-2-(methyl)-propionylamino]ethoxy}-2-methylphenyl)methyl]-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one and acetobromo-α-D-galactose instead of 4-{[4-(3-benzyloxypropoxy)phenyl]methyl}-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one and acetobromo-α-D-glucose, respectively.
Sources & evidence
- ORD record
- ord-3528304e585b4354aa8e2c6a9cae279a
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635684B2
Reaction notes
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