反応 #344620

反応方程式

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

溶媒

isopropanol

water

反応条件

後処理

1. 1
   温度Heat
2. 2
   温度at reflux for 38 minutes
3. 3
   温度cool
4. 4
   ろ過filter
5. 5
   洗浄Rinse the zinc dust
6. 6
   workup.ADDITIONwith a mixture of ethyl acetate/water
7. 7
   ろ過filter
8. 8
   workup.ADDITIONdilute the filtrate with water
9. 9
   抽出Extract with a mixture of ethyl acetate/cyclohexane (3×)
10. 10
    洗浄wash the combined organic extracts with water
11. 11
    その他Evaporate the solvent in vacuo

実験手順

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.

出典