Potassium Carbonate → HCID 57213173, compound

HRID 258446Notes

Reaction equation

HRID 258446 reaction equation
C([O:4][C@@H:5]([C@H:21]([O:37]C(=O)C)[C@H:22]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:23][CH:24]([O:27][CH3:28])[O:25][CH3:26])[C@H:6]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7][CH:8]([O:11][CH3:12])[O:9][CH3:10])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:14]([O:13][C@@H:6]([C@H:5]([OH:4])[C@@H:21]([OH:37])[C@H:22]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:23][CH:24]([O:27][CH3:28])[O:25][CH3:26])[CH2:7][CH:8]([O:9][CH3:10])[O:11][CH3:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57306737HCID 57306737, compound

Product 1

HCID 57213173HCID 57213173, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 100 ml of methanol were added 9.76 g (17.4 mM) of (3R,4R,5R,6R) 4,5-diacetoxy-3,6-dibenzyloxy-1,1,8,8-tetramethoxyoctane [20] obtained via the same route as described above and 6.17 g (43.5 mM) of potassium carbonate. The mixture was heated for 2 hours under reflux while stirring. After it was confirmed by thin layer chromatography that the reaction was completed, the solvent was distilled off under reduced pressure. Water was added to the residue and the mixture was extracted with diethyl ether. After the extract was washed with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 7.55 g (15.8 mM) of (3R,4R, 5R,6R) 3,6-dibenzyloxy-1,1,8,8-tetramethoxyoctane-4,5-diol [21]. Yield, 91%.

Workup

  1. customobtained via the same route
  2. temperatureThe mixture was heated for 2 hours
  3. temperatureunder reflux
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with diethyl ether
  7. washAfter the extract was washed with saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9bb7a79579534ebf9a0fd9341a5d1302
Source dataset
uspto-grants-1993_11
Patent number
US05266703

Reaction notes

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