Sodium Dithionite → HCID 57723960, compound

HRID 1987687Notes

Reaction equation

HRID 1987687 reaction equation
[CH3:1][C:2]1([CH3:12])O[C@H:6]2C=CC[O:11][C@H:5]2[CH2:4][O:3]1.C[N+]1([O-])CC[O:17]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[O-][Si]([O-])=O.[Mg+2].C1COCC1.[C:39]([OH:43])([CH3:42])([CH3:41])C.[OH2:44]>O=[Os](=O)(=O)=O.O>[CH3:1][C:2]1([CH3:12])[O:3][C@H:4]2[C@H:41]([OH:17])[C@H:39]([OH:43])[CH2:42][O:11][C@H:5]2[CH2:6][O:44]1

Participants

8

Reactant 5

HCID 24489Sodium DithioniteHCID 61680MAGNESIUM SILICATE (synthetic)HCID 82029Methyl morpholine oxideHCID 22124471t-Butanol tetrahydrofuran waterHCID 57723925HCID 57723925, compound

Product 1

HCID 57723960HCID 57723960, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a solution of optically pure (4aS,8aS)-2,2-dimethyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine (48 mg, 0.28 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. Sodiumhydrosulphite (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-02bd7fb969a14248af6a2544b3550648
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

Loading…