alpha-D-Glucopyranosyl bromide, tetraacetate → 4-{[4-Benzyloxy-2-(tetrahydro-4H-pyran-4-yloxy)phenyl]-methyl}-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazole

HRID 2223665Notes

Reaction equation

HRID 2223665 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[C:17](=[O:24])[NH:18][NH:19][C:20]=2[CH:21]([CH3:23])[CH3:22])=[C:11]([O:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]([O:38][C@@H:39]1[C@@H:44]([O:45][C:46](=[O:51])[C:47]([CH3:50])([CH3:49])[CH3:48])[C@H:43]([O:52][C:53](=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55])[C@@H:42]([CH2:59][O:60][C:61](=[O:66])[C:62]([CH3:65])([CH3:64])[CH3:63])[O:41][C@@H:40]1Br)(=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34].CC(OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O)=O>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[C:17]([O:24][C@@H:40]3[O:41][C@H:42]([CH2:59][O:60][C:61](=[O:66])[C:62]([CH3:65])([CH3:64])[CH3:63])[C@@H:43]([O:52][C:53](=[O:58])[C:54]([CH3:55])([CH3:56])[CH3:57])[C@H:44]([O:45][C:46](=[O:51])[C:47]([CH3:48])([CH3:49])[CH3:50])[C@H:39]3[O:38][C:32](=[O:37])[C:33]([CH3:36])([CH3:34])[CH3:35])=[N:18][NH:19][C:20]=2[CH:21]([CH3:23])[CH3:22])=[C:11]([O:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 10886360((2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl)methyl 2,2-dimethylpropanoateHCID 685376674-{[4-benzyloxy-2-(tetrahydro-4H-pyran-4-yloxy)phenyl]methyl}-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one

Product 1

HCID 866020304-{[4-Benzyloxy-2-(tetrahydro-4H-pyran-4-yloxy)phenyl]-methyl}-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazole

Procedure

The title compound was prepared in a similar manner to that described in Reference Example 12 using 4-{[4-benzyloxy-2-(tetrahydro-4H-pyran-4-yloxy)phenyl]methyl}-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one and 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide instead of 4-{[4-(2-benzyloxycarbonyl-2-methylpropoxy)phenyl]methyl}-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one and acetobromo-α-D-glucose, respectively.

Sources & evidence

ORD record
ord-eb8822c51a7140d9ad8e4db1a334666c
Source dataset
uspto-grants-2008_05
Patent number
US07375087B2

Reaction notes

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