Hydrogen Peroxide → HCID 66968973, compound

HRID 1359925Notes

Reaction equation

HRID 1359925 reaction equation
[CH2:1]([C:3]1[CH:49]=[CH:48][C:6]([CH2:7][C:8]2[CH:9]=[C:10]([C:24]3([O:42][C@H:41]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[C@@H:36]([O:37][C:38](=[O:40])[CH3:39])[C@H:31]([O:32][C:33](=[O:35])[CH3:34])[C@H:26]3[O:27][C:28](=[O:30])[CH3:29])O)[CH:11]=[C:12](B3OC(C)(C)C(C)(C)O3)[C:13]=2[CH3:14])=[CH:5][CH:4]=1)[CH3:2].OO.C(OCC)(=[O:54])C.[OH2:58]>C(O)(=O)C>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[C:13]([CH3:14])=[C:12]([OH:54])[CH:11]=[C:10]([C:24]3([O:42][C@H:41]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[C@@H:36]([O:37][C:38](=[O:40])[CH3:39])[C@H:31]([O:32][C:33](=[O:35])[CH3:34])[C@H:26]3[O:27][C:28](=[O:30])[CH3:29])[OH:58])[CH:9]=2)=[CH:48][CH:49]=1)[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 8857Ethyl AcetateHCID 66968975HCID 66968975, compound

Product 1

HCID 66968973HCID 66968973, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(4-ethylbenzyl)-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene (0.64 g) in acetic acid (3 mL) is treated with hydrogen peroxide solution (0.2 mL, 35% in water) for 3 h. Then, ethyl acetate and water are added. The organic layer is separated and washed with aqueous NaHCO3 solution, water and brine. After drying (magnesium sulphate) of the organic solution, the solvent is removed under reduced pressure and the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 2:1->1:2).

Workup

  1. customThe organic layer is separated
  2. washwashed with aqueous NaHCO3 solution, water and brine
  3. dry with materialAfter drying (magnesium sulphate) of the organic solution
  4. customthe solvent is removed under reduced pressure
  5. customthe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 2:1->1:2)

Sources & evidence

ORD record
ord-05e2f603f3bd4eb49c81623bdf2d085b
Source dataset
uspto-grants-2011_02
Patent number
US07879807B2

Reaction notes

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