Water → HCID 57723927, compound

HRID 1987685Notes

Reaction equation

HRID 1987685 reaction equation
C[N+]1([O-])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[O-][Si]([O-])=O.[Mg+2].[OH2:22].C1C[O:26][CH2:25][CH2:24]1.[C:28]([OH:32])([CH3:31])([CH3:30])C.[OH2:33]>O=[Os](=O)(=O)=O>[CH3:31][C:28]1([CH3:30])[O:32][C@@H:24]2[C@@H:25]([OH:26])[C@@H:7]([OH:33])[CH2:6][O:5][C@H:4]2[CH2:3][O:22]1

Participants

7

Reactant 5

HCID 962WaterHCID 24489Sodium DithioniteHCID 61680MAGNESIUM SILICATE (synthetic)HCID 82029Methyl morpholine oxideHCID 22124471t-Butanol tetrahydrofuran water

Product 1

HCID 57723927HCID 57723927, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of optically pure (4aS,8aR-2,2-dimethyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine (50 mg, 0.29 mmol) in 4.5 mL of THF-tert-BuOH-H2O (1:3:0.5) was added NMO (45 mg, 0.32 mmol) and the solution was stirred for 5 min. at ambient temperature. OsO4 (15 μL, 25 wt % In tert-BuOH) was added and the solution was stirred at ambient temperature for 4 days. Sodium hydrosulphite (0.2 g), Florisil (2.0 g) and H2O (5 ml) were added and the mixture was stirred for 30 min, wash with acetone (100 mL), filtered through filter paper and extracted with EtOAc (80 mL×2). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography with 100% EtOAc.

Workup

  1. stirringthe solution was stirred at ambient temperature for 4 days
  2. stirringthe mixture was stirred for 30 min
  3. washwash with acetone (100 mL)
  4. filtrationfiltered
  5. filtrationthrough filter paper
  6. extractionextracted with EtOAc (80 mL×2)
  7. washThe combined organic layers were washed with brine (50 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography with 100% EtOAc

Sources & evidence

ORD record
ord-d6432347fe31456ebf1decec6e5364e9
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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