alpha-D-Glucopyranosyl bromide, tetraacetate → 4-[(4-Ethylphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

HRID 457513Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11](=[O:16])[NH:12][NH:13][C:14]=2[CH3:15])=[CH:5][CH:4]=1)[CH3:2].[CH3:17][C:18]([O:20][CH2:21][C@H:22]1[O:27][C@H:26](Br)[C@H:25]([O:29][C:30]([CH3:32])=[O:31])[C@@H:24]([O:33][C:34]([CH3:36])=[O:35])[C@@H:23]1[O:37][C:38]([CH3:40])=[O:39])=[O:19]>O1CCCC1.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]2[C:11]([O:16][C@@H:26]3[O:27][C@H:22]([CH2:21][O:20][C:18](=[O:19])[CH3:17])[C@@H:23]([O:37][C:38](=[O:39])[CH3:40])[C@H:24]([O:33][C:34](=[O:35])[CH3:36])[C@H:25]3[O:29][C:30](=[O:31])[CH3:32])=[N:12][NH:13][C:14]=2[CH3:15])=[CH:7][CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 4-[(4-ethylphenyl)methyl]-5-methyl-1,2-dihydro-3H-pyrazol-3-one (0.65 g) and acetobromo-α-D-glucose (1.2 g) in tetrahydrofuran (15 mL) was added silver carbonate (0.83 g), and the mixture was stirred at 60° C. overnight under light shielding. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran), and successively by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/3) to give 4-[(4-ethylphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.61 g).

Workup

customThe reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran)

Sources & evidence

ORD record: ord-80191eb713a3491e9f19c7bd5944fa19
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189702B2

Reaction notes

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