تفاعل #74492

معادلة التفاعل

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

المردود 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

المردود 35.0%

المذيبات

water

water

water

ظروف التفاعل

المعالجة

1. 1
   تجفيفNormal work-up with CH2Cl2 and drying with MgSO4
2. 2
   أخرىWithout further purification, it
3. 3
   أخرىwas reacted with POCl3 (2 ml) in toluene (20 ml)
4. 4
   درجة الحرارةunder refluxed condition
5. 5
   أخرىAfter reaction complete
6. 6
   أخرىAfter work-up with CH2Cl2, organic layer was evaporated under reduced pressure
7. 7
   أخرىThe residue was purified with use of column chromatography (Hexane/EtOAc=½)

الإجراء التجريبي

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.

المصدر