alpha-D-Glucopyranosyl bromide, tetraacetate → HCID 68538715, compound

HRID 1442451Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10](=[O:17])[NH:11][NH:12][C:13]=2[CH:14]([CH3:16])[CH3:15])=[C:4]([F:18])[CH:3]=1.[CH3:19][C:20]([O:22][CH2:23][C@H:24]1[O:29][C@H:28](Br)[C@H:27]([O:31][C:32]([CH3:34])=[O:33])[C@@H:26]([O:35][C:36]([CH3:38])=[O:37])[C@H:25]1[O:39][C:40]([CH3:42])=[O:41])=[O:21].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:32]([O:31][C@@H:27]1[C@@H:26]([O:35][C:36](=[O:37])[CH3:38])[C@@H:25]([O:39][C:40](=[O:41])[CH3:42])[C@@H:24]([CH2:23][O:22][C:20](=[O:21])[CH3:19])[O:29][C@H:28]1[O:17][C:10]1[C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[F:18])=[C:13]([CH:14]([CH3:16])[CH3:15])[NH:12][N:11]=1)(=[O:33])[CH3:34]

Participants

Reactant 3

HCID 101776alpha-D-Glucopyranosyl bromide, tetraacetate

HCID 2734143alpha-Acetobromogalactose

HCID 68538657HCID 68538657, compound

Product 1

HCID 68538715HCID 68538715, compound

Procedure

The title compound was prepared in a similar manner to that described in Reference Example 12 using 4-[(4-bromo-2-fluorophenyl)methyl]-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one and acetobromo-α-D-galactose 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-aaa1ad5666024509ba05aabd72a69073
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655632B2

Reaction notes

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