(2S,3R,4S,5R)-2,3,4,5-Tetrahydroxycyclohexanone → HCID 44511908, compound

HRID 389373Notes

Reaction equation

HRID 389373 reaction equation
[CH2:1]1[C:6](=[O:7])[C@@H:5]([OH:8])[C@H:4]([OH:9])[C@@H:3]([OH:10])[C@@H:2]1O>O>[OH:10][C@@H:3]1[C@@H:4]([OH:9])[C@H:5]([OH:8])[C:6](=[O:7])[CH:1]=[CH:2]1

Participants

3

Reactant 1

HCID 10583108(2S,3R,4S,5R)-2,3,4,5-Tetrahydroxycyclohexanone

Product 1

HCID 44511908HCID 44511908, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.64 g of 2-deoxy-scyllo-inosose synthesized according to the method described in WO 2006/112000 and 5 mL of an ion exchange resin IR120B were added to 13.6 mL of water, and the resulting mixture was heated at reflux for 20 hours. After the completion of the reaction, the ion exchange resin was filtered and the filtrate was concentrated under a reduced pressure. The condensation residue was purified with silica gel column (ethyl acetate), whereby 604 mg (yield: 41%) of (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one was obtained.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 20 hours
  3. customAfter the completion of the reaction
  4. filtrationthe ion exchange resin was filtered
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. customThe condensation residue was purified with silica gel column (ethyl acetate)

Sources & evidence

ORD record
ord-0b6e73355eb044b994887eabe1c841a7
Source dataset
uspto-grants-2013_02
Patent number
US08378146B2

Reaction notes

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