Multi-step reaction with 12 steps
1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C / Inert atmosphere
2: osmium(VIII) oxide; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); methanesulfonamide; sodium hydrogencarbonate; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 6 h / 5 °C / Inert atmosphere
3: nitrogen; methylamine / water / 1 h / 50 °C / 10 Torr / Inert atmosphere
4: sodium hydrogencarbonate / ethyl acetate / 1.5 h / Inert atmosphere
5: dmap; triethylamine; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.03 h / 0 - 20 °C / Inert atmosphere
6: dichloromethane / 1 h / -40 °C / Inert atmosphere
7: caesium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C / Inert atmosphere
8: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / Inert atmosphere
9: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
10: acetic acid / chloroform / 12 h / 20 °C / Molecular sieve; Inert atmosphere
11: sodium cyanoborohydride / tetrahydrofuran / 2 h / Inert atmosphere
12: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
With
1H-imidazole; dmap; osmium(VIII) oxide; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); methanesulfonamide; nitrogen; tetrabutyl ammonium fluoride; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; methylamine; potassium hexacyanoferrate(III);
In
tetrahydrofuran; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/chem.201003489