Sodium Thiosulfate → HCID 89975559, compound

HRID 716159Notes

Reaction equation

HRID 716159 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[CH3:23][S:24]([O:27][C@@H:28]([C@@H:30]1[C@H:34]([CH2:35][OH:36])[O:33][C:32]([CH3:38])([CH3:37])[O:31]1)[CH3:29])(=[O:26])=[O:25].C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.C(OCC)(=O)C.N1C=CC=CC=1>[CH3:23][S:24]([O:27][C@@H:28]([C@@H:30]1[C@H:34]([CH:35]=[O:36])[O:33][C:32]([CH3:37])([CH3:38])[O:31]1)[CH3:29])(=[O:25])=[O:26]

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 89975550HCID 89975550, compound

Product 1

HCID 89975559HCID 89975559, compoundYield 95.2%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3 g of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1H)-one (Dess-Martin Periodinane) was added to a solution of 1.8 g of (1R)-1-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-yl)ethyl methanesulfonate (which contained fluorotris(propan-2-yl)silane) and 1.16 mL of pyridine in 20 mL of dichloromethane at a temperature of 5° C. to 10° C., and the obtained mixture was then stirred at room temperature for 2 hours. Thereafter, ethyl acetate, a saturated sodium hydrogen carbonate aqueous solution and a sodium thiosulfate aqueous solution were added to the reaction mixture. The organic layer was fractionated, and it was successively washed with water and a saturated sodium chloride aqueous solution and was then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, so as to obtain 1.7 g of (1R)-1-((4S,5R)-5-formyl-2,2-dimethyl-1,3-dioxolane-4-yl)ethyl methanesulfonate in the form of a yellow oily product.

Workup

  1. washit was successively washed with water
  2. dry with materiala saturated sodium chloride aqueous solution and was then dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-256cef39e69644bcbf59435bce436e78
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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