Multi-step reaction with 7 steps
1.1: tetrabutylammomium bromide; sodium hydride / tetrahydrofuran / 0.5 h / 0 °C
1.2: 0 - 20 °C
2.1: potassium osmate(VI) dihydrate; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 24 h / 0 °C
3.1: pyridine / dichloromethane / 2 h / -70 °C
4.1: acetic acid / water / 1.5 h / 50 °C
5.1: sodium periodate / acetone / 1.5 h / 25 °C
6.1: dmap / dichloromethane / 16 h / 25 °C
7.1: sodium bromate; sodium dithionite / ethyl acetate / 6 h / 25 °C
With
pyridine; dmap; potassium osmate(VI) dihydrate; sodium bromate; sodium periodate; sodium dithionite; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); tetrabutylammomium bromide; sodium hydride; potassium carbonate; acetic acid; potassium hexacyanoferrate(III);
In
tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; tert-butyl alcohol;