Hydrogen Peroxide → HCID 20705960, compound

HRID 429741Notes

Reaction equation

HRID 429741 reaction equation
P([O:4][C@H:5]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[C@@H:6]([O:35][C:36](=[O:38])[CH3:37])[C@H:7]([O:31][C:32](=[O:34])[CH3:33])[C@@H:8]([O:27][C:28](=[O:30])[CH3:29])[C:9]([P:11]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12])=[O:10])(O)O.OO>C1COCC1.CCOCC>[CH2:13]([P:11]([C:9]([C@@H:8]([C@H:7]([C@@H:6]([C@@H:5]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[OH:4])[O:35][C:36](=[O:38])[CH3:37])[O:31][C:32](=[O:34])[CH3:33])[O:27][C:28](=[O:30])[CH3:29])=[O:10])([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:12])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 53964925HCID 53964925, compound

Product 1

HCID 20705960HCID 20705960, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound 78 (1.2 g, 2.2 mmol) in THF (50 mL) cooled to −78° C. with a dry ice-acetone bath was added dropwise 30 percent H2O2 (10 mL), and the mixture was allowed to warm up to room temperature, and stirred for 1.5 hours at room temperature. The mixture was diluted with ether and successively washed with ice-cold saturated Na2S2O3, saturated NaHCO3, saturated NaCl, and water. The organic phase was dried over anhydrous Na2SO4 and concentrated to give a α:β (1:4) mixture of Compound 85 (1.36 g, 98 percent) as judged by 1H-NMR (CDCl3). This product was used for the next step without further purification.

Workup

  1. washsuccessively washed with ice-cold saturated Na2S2O3, saturated NaHCO3, saturated NaCl, and water
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customto give a α
  5. customThis product was used for the next step without further purification

Sources & evidence

ORD record
ord-422a71e0b6cc4ebba827b97f18c6ed23
Source dataset
uspto-grants-2001_11
Patent number
US06319695B1

Reaction notes

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