Sodium Thiosulfate → HCID 70128516, compound

HRID 1004339Notes

Reaction equation

HRID 1004339 reaction equation
[OH:1][C@H:2]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C@H:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[O:1]=[C:2]([C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])[CH:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:4][C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86755323HCID 86755323, compound

Product 1

HCID 70128516HCID 70128516, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.5 0 g of 1-benzyl 3-tert-butyl 2-ethyl (1S,2R)-1-hydroxy-1,2,3-propanetricarboxylate in 30 ml of chloroform was stirred with 2.35 g of the Dess-Martin reagent (periodinane) at room temperature for 1.5 hours. The reaction solution was poured into a mixture of saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=9/1] to give 1.37 g of the title compound as a colorless oily substance

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=9/1]

Sources & evidence

ORD record
ord-fbb9a801fd0246a09bf1278cde4938b4
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Reaction notes

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