Sucrose → HCID 14061412, compound

HRID 2351094Notes

Reaction equation

HRID 2351094 reaction equation
C(O)[C@H]1O[C@H](O[C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.[CH2:24]([O:26][C:27]([CH:29]1[C:36](=[O:37])[CH2:35][CH:34]2[CH:30]1[CH2:31][C:32]1([O:41][CH2:40][CH2:39][O:38]1)[CH2:33]2)=[O:28])[CH3:25].CCC(COC(C(N(CC[NH+](C)C)C)=O)(C1C=CC=CC=1)C1C=CC=CC=1)CC.[Cl-]>P([O-])([O-])([O-])=O>[CH2:24]([O:26][C:27]([CH:29]1[C:36](=[O:37])[CH2:35][C@H:34]2[C@@H:30]1[CH2:31][C:32]1([O:38][CH2:39][CH2:40][O:41]1)[CH2:33]2)=[O:28])[CH3:25]

Participants

5

Reactant 3

HCID 5988Sucrose2×HCID 19153X 100HCID 14061410HCID 14061410, compound

Product 1

HCID 14061412HCID 14061412, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 100 ml of 0.1 M phosphate buffer (pH 7) containing sucrose (15 g) was dispersed 7.0 g of baker's yeast at 30° C., and the mixture was shaken at 30° C. for 15 minutes. To the resulting mixture was added an emulsion of 505 mg of (1SR,5RS)-2-ethoxycarbonyl-7,7-ethylenedioxybicyclo[3.3.0]octan-3-one (VIII) in 0.2% Triton X-100 solution (15 ml), and the mixture was shaken at 30° C. After 8 hours, 10 g of sucrose were added to the mixture. After shaking for 24 hours, the reaction mixture was filtered through Celite, the filtrate was saturated with sodium chloride and extracted three times with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (eluting solution: 20% (v/v) diethyl ether/hexane) to obtain 183 mg of oily (1S,5R)-2-ethoxycarbonyl-7,7-ethylenedioxybicyclo[3.3.0]octan-3-one, (IV).

Workup

  1. additionwas dispersed 7.0 g of baker's yeast at 30° C.
  2. stirringthe mixture was shaken at 30° C
  3. waitAfter 8 hours
  4. stirringAfter shaking for 24 hours
  5. filtrationthe reaction mixture was filtered through Celite
  6. extractionextracted three times with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel chromatography (eluting solution: 20% (v/v) diethyl ether/hexane)

Sources & evidence

ORD record
ord-e69a0e254feb4da5a9e2c9da949a9403
Source dataset
uspto-grants-1989_10
Patent number
US04871869

Reaction notes

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