Sodium Dithionite → HCID 12179948, compound

HRID 1987660Notes

Reaction equation

HRID 1987660 reaction equation
C(O[C:4]([C@@H:6]1[C@H:11]([O:12]C(=O)C)C=CC[O:7]1)=[O:5])C.C[N+]1([O-])CC[O:20][CH2:19]C1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[O-][Si]([O-])=O.[Mg+2].[CH2:37]1[CH2:41][O:40][CH2:39][CH2:38]1.[C:42]([OH:46])(C)(C)[CH3:43].[OH2:47]>O=[Os](=O)(=O)=O.O>[CH2:42]([O:46][C:19]([C@@H:38]1[C@H:39]([O:40][C:41](=[O:47])[CH3:37])[C@@H:4]([OH:5])[C@@H:6]([OH:7])[CH2:11][O:12]1)=[O:20])[CH3:43]

Participants

8

Reactant 5

HCID 24489Sodium DithioniteHCID 61680MAGNESIUM SILICATE (synthetic)HCID 82029Methyl morpholine oxideHCID 10242330HCID 10242330, compoundHCID 22124471t-Butanol tetrahydrofuran water

Product 1

HCID 12179948HCID 12179948, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To (2S,3R)-3-acetoxy-3,6-dihydro-2H-pyran-2-carboxylic acid ethyl ester (200 mg, 0.93 mmol) in 18 ml of THF-tert-BuOH—H2O (4:11.8:2) was added NMO (408 mg, 2.98 mmol) and the solution was stirred for 5 min at ambient temperature. OsO4 (0.2 ml, 2.5 wt % in tert-BuOH) was added and the solution was stirred at ambient temperature for 72 H. Sodium hydrosulphite (0.83 g), Florisil (2.0 g) and H2O (2 ml) were added sequentially and the mixture was stirred for 30 minutes, washed with 200 ml EtOAc, filtered through filter paper and the solvent was evaporated. The crude product was purified by flash chromatography with 20-80% EtOAc-hexane to give (2S,3R,4S,5S)-3-acetoxy-4,5-dihydroxy-tetrahydropyran-2-carboxylic acid ethyl ester

Workup

  1. stirringthe solution was stirred at ambient temperature for 72 H
  2. stirringthe mixture was stirred for 30 minutes
  3. washwashed with 200 ml EtOAc
  4. filtrationfiltered
  5. filtrationthrough filter paper
  6. customthe solvent was evaporated
  7. customThe crude product was purified by flash chromatography with 20-80% EtOAc-hexane

Sources & evidence

ORD record
ord-80c2513098354210a4eaa11729692d02
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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