Reaktion #344620

Reaktionsgleichung

methyl-2,3,4-tris(phenylmethoxy)-6-bromo-6-desoxy-α-D-mannopyranose

→

2,3,4-tris(phenylmethoxy)-5,6-dideoxy-D-lyxo-hex-5-enose

Lösungsmittel

isopropanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturHeat
2. 2
   Temperaturat reflux for 38 minutes
3. 3
   Temperaturcool
4. 4
   Filtrationfilter
5. 5
   WaschenRinse the zinc dust
6. 6
   workup.ADDITIONwith a mixture of ethyl acetate/water
7. 7
   Filtrationfilter
8. 8
   workup.ADDITIONdilute the filtrate with water
9. 9
   ExtraktionExtract with a mixture of ethyl acetate/cyclohexane (3×)
10. 10
    Waschenwash the combined organic extracts with water
11. 11
    SonstigeEvaporate the solvent in vacuo

Vorschrift

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.

Quelle