Multi-step reaction with 9 steps
1: 82 percent / ozone / acetone; H2O / 0 - 5 °C
2: 1.)trimethyl phosphite 2.)triethylamine / 1.)85 deg C, 3 h 2.)ethyl acetate, 0-5 deg C, 4h
3: ozone / CH2Cl2; methanol / -25 °C
4: 50 percent / water / methanol; ethyl acetate / 18 h / 22 °C
5: triethylamine / CH2Cl2 / 1 h / 0 - 5 °C
6: 85 percent / thionyl chloride, pyridine / tetrahydrofuran / 0.25 h / -20 °C
7: 88 percent / 2,6-lutidine / tetrahydrofuran / 66 h / 50 °C
8: 72 percent / hydroquinone / toluene / 48 h / 100 °C
9: phosphate buffer (pH 7), hydrogen / Pd/C (10percent) / tetrahydrofuran; H2O / 1.5 h / 2327.2 Torr / Ambient temperature
With
pyridine; 2,6-dimethylpyridine; thionyl chloride; phosphate buffer; water; hydrogen; ozone; triethylamine; hydroquinone; phosphorous acid trimethyl ester;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene;
DOI:10.1139/v88-225