تفاعل #2390638

معادلة التفاعل

compound

3-(Naphth-2-ylmethyl)- 3,3a,6,6a-tetrahydro-cyclopenta[b]furan-2-one

N-methylmorpholine N-oxide

acetone

→

4,5-Dihydroxy-3-(naphth-2-ylmethyl)-hexahydro-cyclopenta[b]furan-2-one

المذيبات

tert-butanol

ظروف التفاعل

المعالجة

1. 1
   تركيزThe mixture was concentrated
2. 2
   أخرىthe residue was chromatographed over silica gel (mobile phase: dichloromethane/methanol (100:4))

الإجراء التجريبي

200 mg (0.75 mmol) of the compound from Example 7, 0.08 ml of a 2.5% strength osmium tetroxide solution in tert-butanol and 180 mg of N-methylmorpholine N-oxide were dissolved in 2.5 ml of acetone and stirred at RT for 15 h. The mixture was concentrated and the residue was chromatographed over silica gel (mobile phase: dichloromethane/methanol (100:4)). Yield: 161 mg of a diastereomer mixture. Diastereomer ratio: 1:5:5:1 (HPLC). MS (DCI/NH3): m/e=316 (M+NH4)

المصدر