Hydrogen Peroxide → HCID 20705960, compound

HRID 2056323Notes

Reaction equation

HRID 2056323 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-cb2e26ff613d4c84b4533d15a91b2716
Source dataset
uspto-grants-2008_02
Patent number
US07335500B2

Reaction notes

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