1: 285 mg / DMAP; NEt3 / tetrahydrofuran; toluene / 90 h / 20 °C 2: 4-methylmorpholine N-oxide; OsO4 / CH2Cl2; H2O; 2-methyl-propan-2-ol / 0.75 h 3: 409.1 mg / Pb(OAc)4 / CH2Cl2; H2O; 2-methyl-propan-2-ol / 0.17 h 4: 77 percent / KMnO4 / diethyl ether; aq. phosphate buffer; 2-methyl-propan-2-ol / 0.08 h / 20 °C / pH 7.4 5: 17 percent / NaOH / methanol / 20 °C View Scheme

ozone anschliessend mit wss.Wasserstoffperoxid;

1.1: 285 mg / DMAP; NEt3 / tetrahydrofuran; toluene / 90 h / 20 °C 2.1: 4-methylmorpholine N-oxide; OsO4 / CH2Cl2; H2O; 2-methyl-propan-2-ol / 0.75 h 3.1: Pb(OAc)4 / CH2Cl2; H2O; 2-methyl-propan-2-ol / 0.17 h 3.2: aldolase antibody 38C2 / aq. phosphate buffer / pH 7.4 4.1: KMnO4 / diethyl ether; aq. phosphate buffer; 2-methyl-propan-2-ol / 0.08 h / 20 °C / pH 7.4 5.1: NaOH / methanol / 20 °C View Scheme