Phosphate → HCID 21914222, compound

HRID 1274484Notes

Reaction equation

HRID 1274484 reaction equation
[CH3:1][C:2]([CH:6]1[CH2:11][CH2:10][O:9][C:8]([CH3:13])([CH3:12])[O:7]1)([CH3:5])[CH:3]=C.P([O-])([O-])([O-])=[O:15]>C1COCC1.O=[Os](=O)(=O)=O>[CH3:12][C:8]1([CH3:13])[O:7][CH:6]([C:2]([CH3:1])([CH3:5])[CH:3]=[O:15])[CH2:11][CH2:10][O:9]1

Participants

5

Reactant 2

HCID 1061PhosphateHCID 22121316HCID 22121316, compound

Product 1

HCID 21914222HCID 21914222, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

286 mg (1.55 mmol) of acetonide 44 is dissolved in 18 ml of THF, and 14 ml of aqueous phosphate buffer at pH 7 is added. 400 μl (0.031 mol, 0.02 equivalent) of OsO4 solution (2.5% in tert-butanol) is added in drops to the reaction mixture that is stirred vigorously. After 10 minutes, 996 mg (4.656 mmol, 3 equivalents) of NalO4 is added in portions over a period of 20 minutes. The mixture is stirred vigorously at room temperature and, after 24 and 48 hours in each case, another 332 mg (1.55 mmol, 2×1.0 equivalents each) of NalO4 is added. After 55 hours, the phases are separated, the aqueous phase is extracted with ether, the combined organic phases are dried on MgSO4 and concentrated by evaporation. The residue is purified by column chromatography with pentane:DE=1:1. 221 mg (1.19 mmol) of aldehyde 45 corresponding to a yield of 76% is obtained.

Workup

  1. addition996 mg (4.656 mmol, 3 equivalents) of NalO4 is added in portions over a period of 20 minutes
  2. stirringThe mixture is stirred vigorously at room temperature
  3. additionafter 24 and 48 hours in each case, another 332 mg (1.55 mmol, 2×1.0 equivalents each) of NalO4 is added
  4. waitAfter 55 hours
  5. customthe phases are separated
  6. extractionthe aqueous phase is extracted with ether
  7. customthe combined organic phases are dried on MgSO4
  8. concentrationconcentrated by evaporation
  9. customThe residue is purified by column chromatography with pentane

Sources & evidence

ORD record
ord-235643d73c494e599ed981f26da7443b
Source dataset
uspto-grants-2000_12
Patent number
US06156905

Reaction notes

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