反应详情

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.

1. dry with materialNormal work-up with CH2Cl2 and drying with MgSO4
2. customWithout further purification, it
3. customwas reacted with POCl3 (2 ml) in toluene (20 ml)
4. temperatureunder refluxed condition
5. customAfter reaction complete
6. customAfter work-up with CH2Cl2, organic layer was evaporated under reduced pressure
7. customThe residue was purified with use of column chromatography (Hexane/EtOAc=½)