Реакция #74489

Уравнение реакции

3-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-7-methylbenzo[e][1,2,4]triazine

TMSI

→

title compound

Выход 52.0%

(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((7-methylbenzo[e][1,2,4]triazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Выход 52.0%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   ДругоеAfter quenching
2. 2
   Другоеthe reaction with methanol, solvent
3. 3
   Другоеwas evaporated under reduced pressure
4. 4
   ДругоеThe residue was purified with silica gel (10% MeOH in CH2Cl2)

Методика

3-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-7-methylbenzo[e][1,2,4]triazine (115 mg, 0.15 mmol) in acetonitrile (10 ml) reacted with TMSI (146 mg, 0.73 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 day. After quenching the reaction with methanol, solvent was evaporated under reduced pressure. The residue was purified with silica gel (10% MeOH in CH2Cl2) to afford title compound (33 mg, 52% yield) as a light yellow solid.

Источник