Hydrogen Peroxide → HCID 59235333, compound

HRID 2174335Notes

Reaction equation

HRID 2174335 reaction equation
[Cl:1][C:2]1[C:3]([CH2:49][C:50]2[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=2)=[CH:4][C:5]([C@H:10]2[C@H:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@H:14]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@H:13]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@@H:12]([CH2:40][O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:11]2)=[C:6]([CH:9]=1)[CH:7]=[O:8].OO.Cl([O-])(=O)(=O)=[O:61].[Na+]>CC(O)(C)C.O>[Cl:1][C:2]1[C:3]([CH2:49][C:50]2[CH:51]=[CH:52][C:53]([CH2:56][CH3:57])=[CH:54][CH:55]=2)=[CH:4][C:5]([C@H:10]2[C@H:15]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C@@H:14]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@H:13]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@@H:12]([CH2:40][O:41][CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[O:11]2)=[C:6]([CH:9]=1)[C:7]([OH:61])=[O:8]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 522606Sodium PerchlorateHCID 59235323HCID 59235323, compound

Product 1

HCID 59235333HCID 59235333, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

To a solution of 5-chloro-4-(4-ethylbenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzaldehyde (0.826 g, 1.1 mmol) in t-BuOH/water (3:1, 17 mL) was added hydrogen peroxide (30%, 5.29 mL, 46.7 mmol) and sodium perchlorate (0.14 g, 1.1 mmol), and the solution was stirred overnight at RT. The volatiles were removed under reduced pressure, and the residue was quenched with water. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, washed with water and then with brine, and then dried over anhydrous sodium sulfate. After removal of the volatiles, 0.802 g of crude solid product was obtained. MS ESI− (m/z): 841 (M+45)−.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was quenched with water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialwith brine, and then dried over anhydrous sodium sulfate
  6. customAfter removal of the volatiles

Sources & evidence

ORD record
ord-2c1b68e3af494c92bb930e2a3ec379b0
Source dataset
uspto-grants-2015_06
Patent number
US09061060B2

Reaction notes

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