2,6-di-tert-butyl-4-methylpyridine in dichloromethane T=0°C; 3.5 h;

1: 31-(trimethylsilylether)rapamycin With 3,5-dimethyl pyridine in dichloromethane T=0 - 5°C; 1.08333 h; Inert atmosphere; 2: dimethylphosphoryl chloride in dichloromethane T=0 - 5°C; 1 h; Inert atmosphere;

1.1: sulfuric acid; water / ethyl acetate / 2 h / 0 - 5 °C 2.1: 3,5-dimethyl pyridine / dichloromethane / 1.08 h / 0 - 5 °C / |Inert atmosphere 2.2: 1 h / 0 - 5 °C / |Inert atmosphere View Scheme

1.1: 3,5-dimethyl pyridine / dichloromethane / 1.17 h / 0 - 5 °C / |Inert atmosphere 1.2: 1 h / 0 - 5 °C / |Inert atmosphere 2.1: sulfuric acid; water / tetrahydrofuran / -5 - 0 °C View Scheme

1.1: 3,5-dimethyl pyridine / dichloromethane / 1.08 h / 0 - 5 °C / |Inert atmosphere 1.2: 1 h / 0 - 5 °C / |Inert atmosphere 2.1: 1H-imidazole / dichloromethane / 3 h / 0 - 5 °C 3.1: acetic acid; water / tetrahydrofuran / 2.5 h / 5 °C 4.1: 3,5-dimethyl pyridine / dichloromethane / 1.17 h / 0 - 5 °C / |Inert atmosphere 4.2: 1 h / 0 - 5 °C / |Inert atmosphere 5.1: sulfuric acid; water / tetrahydrofuran / -5 - 0 °C View Scheme

1.1: 1H-imidazole / dichloromethane / 3 h / 0 - 5 °C 2.1: acetic acid; water / tetrahydrofuran / 2.5 h / 5 °C 3.1: 3,5-dimethyl pyridine / dichloromethane / 1.17 h / 0 - 5 °C / |Inert atmosphere 3.2: 1 h / 0 - 5 °C / |Inert atmosphere 4.1: sulfuric acid; water / tetrahydrofuran / -5 - 0 °C View Scheme

1.1: acetic acid; water / tetrahydrofuran / 2.5 h / 5 °C 2.1: 3,5-dimethyl pyridine / dichloromethane / 1.17 h / 0 - 5 °C / |Inert atmosphere 2.2: 1 h / 0 - 5 °C / |Inert atmosphere 3.1: sulfuric acid; water / tetrahydrofuran / -5 - 0 °C View Scheme