alpha-D-Glucopyranosyl bromide, tetraacetate → 5-isopropyl-4-(2-benzyloxybenzyl)-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

HRID 1351094Notes

Reaction equation

HRID 1351094 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][CH:22]=[CH:21][C:10]=1[CH2:11][C:12]1[C:13](=[O:20])[NH:14][NH:15][C:16]=1[CH:17]([CH3:19])[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][C:26]([O:28][CH2:29][C@H:30]1[O:35][C@H:34](Br)[C@H:33]([O:37][C:38]([CH3:40])=[O:39])[C@@H:32]([O:41][C:42]([CH3:44])=[O:43])[C@@H:31]1[O:45][C:46]([CH3:48])=[O:47])=[O:27]>C(#N)C.C(=O)([O-])[O-].[Ag+2]>[CH:17]([C:16]1[NH:15][N:14]=[C:13]([O:20][C@@H:34]2[O:35][C@H:30]([CH2:29][O:28][C:26](=[O:27])[CH3:25])[C@@H:31]([O:45][C:46](=[O:47])[CH3:48])[C@H:32]([O:41][C:42](=[O:43])[CH3:44])[C@H:33]2[O:37][C:38](=[O:39])[CH3:40])[C:12]=1[CH2:11][C:10]1[CH:21]=[CH:22][CH:23]=[CH:24][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 229321724-[(2-benzyloxyphenyl)methyl]-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one

Product 1

HCID 695166955-isopropyl-4-(2-benzyloxybenzyl)-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4-(2-benzyloxybenzyl)-5-isopropyl-1,2-dihydropyrazol-3-one (114 mg) and acetobromo-α-D-glucose (173 mg) in acetonitrile (2 mL) was added silver carbonate (127 mg), and the mixture was stirred under shading the light at room temperature for 3 days. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate/hexane=1/1) to give 5-isopropyl-4-(2-benzyloxybenzyl)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole. To a solution of 5-isopropyl-4-(2-benzyloxybenzyl)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole in tetrahydrofuran (1 mL) and methanol (0.5 mL) was added sodium methoxide (28% methanol solution, 50 μL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1) to give the title compound (22 mg).

Workup

  1. customat room temperature
  2. customfor 3 days
  3. customThe reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-cc16a9e7f7ed4cd69a3a8477d66ccf1d
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

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