HCID 131718248, compound → HCID 86747369, compound

HRID 257438Notes

Reaction equation

HRID 257438 reaction equation
C[C@@:2]1(O[C@H:10]([CH2:12]Br)[C@@:8]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:9])[C@:6]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([OH:7])[C@:4]1([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[OH:5])[OH:3]>C(O)(C)C.O.[Zn]>[C:32]1([CH2:31][O:30][C@@:4]([C@:6]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C@@:8]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([CH:10]=[CH2:12])[OH:9])[OH:7])([OH:5])[CH:2]=[O:3])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 1

HCID 131718248HCID 131718248, compound

Product 1

HCID 86747369HCID 86747369, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Mix methyl-2,3,4-tris(phenylmethoxy)-6-bromo-6-desoxy-α-D-mannopyranose (20.968 g, 39.75 mmol) and activated zinc dust (20.50 g, 314 mmol) in isopropanol (300 mL) and water (55 mL). Heat at reflux for 38 minutes, cool and filter. Rinse the zinc dust with a mixture of ethyl acetate/water, filter and dilute the filtrate with water. Extract with a mixture of ethyl acetate/cyclohexane (3×) and wash the combined organic extracts with water. Evaporate the solvent in vacuo to give 2,3,4-tris(phenylmethoxy)-5,6-dideoxy-D-lyxo-hex-5-enose.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 38 minutes
  3. temperaturecool
  4. filtrationfilter
  5. washRinse the zinc dust
  6. additionwith a mixture of ethyl acetate/water
  7. filtrationfilter
  8. additiondilute the filtrate with water
  9. extractionExtract with a mixture of ethyl acetate/cyclohexane (3×)
  10. washwash the combined organic extracts with water
  11. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-f9c785f9c18b4a7d9ce8068c58b3b9ca
Source dataset
uspto-grants-1993_11
Patent number
US05262425

Reaction notes

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