반응 #74492

반응 방정식

Et2O

3-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-4,5-dihydro-1,2,4-triazin-6(1H)-one

compound 55

3-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-4,5-dihydro-1,2,4-triazin-6(1H)-one

CH2Cl2

DDQ

→

title compound

수율 35.0%

6-Chloro-3-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-1,2,4-triazine

수율 35.0%

용매

water

water

water

반응 조건

후처리

1. 1
   건조Normal work-up with CH2Cl2 and drying with MgSO4
2. 2
   기타Without further purification, it
3. 3
   기타was reacted with POCl3 (2 ml) in toluene (20 ml)
4. 4
   온도under refluxed condition
5. 5
   기타After reaction complete
6. 6
   기타After work-up with CH2Cl2, organic layer was evaporated under reduced pressure
7. 7
   기타The residue was purified with use of column chromatography (Hexane/EtOAc=½)

실험 절차

The 3-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-4,5-dihydro-1,2,4-triazin-6(1H)-one (compound 55, 826 mg, 1.11 mmol) in a mixture of CH2Cl2 (20 ml) and water (2 ml) treated with DDQ (504 mg, 2.22 mmol) at 0° C. After 3 hours, Et2O and water were added to the reaction mixture. Normal work-up with CH2Cl2 and drying with MgSO4 generated crude title compound. Without further purification, it was reacted with POCl3 (2 ml) in toluene (20 ml) under refluxed condition. After reaction complete, the resulting solution was poured into iced water (50 ml). After work-up with CH2Cl2, organic layer was evaporated under reduced pressure. The residue was purified with use of column chromatography (Hexane/EtOAc=½) to provide title compound (296 mg, 35% overall yield) as yellow oil.

출처