Water → 2'-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-(methoxycarbonylmethoxy)acetophenone

HRID 230892

Reaction equation

HRID 230892 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[C:26]=1[C:32](=[O:34])[CH3:33])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:42][C:43]([O:45][CH3:46])=[O:44].O>CN(C)C=O>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:42][C:43]([O:45][CH3:46])=[O:44])[C:26]=1[C:32](=[O:34])[CH3:33])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 105527942'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenone

Product 1

HCID 671359432'-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-(methoxycarbonylmethoxy)acetophenone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2′-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6′-hydroxyacetophenone (0.6 g) in N,N-dimethylformamide (5 mL) were added potassium carbonate (0.26 g) and methyl bromoacetate (0.13 mL), and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into water, and the precipitated crystals were collected by filtration. The crystals were washed with water and dried under reduced pressure to give the title compound (0.62 g).

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washThe crystals were washed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-ce29af43ecdd456797ca97aced649fad
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Linked notes

Loading…