Multi-step reaction with 10 steps
1: 1N aq. NaOH / dioxane / 3 h / Ambient temperature
2: H2SO4 / CH2Cl2
3: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
4: 1,3-dicyclohexylcarbodiimide / CH2Cl2
5: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
6: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
7: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature
8: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h
9: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h
10: diethyl phosphorocyanidate, Et3N / dimethylformamide
With
sodium hydroxide; diethyl cyanophosphonate; sulfuric acid; hydrogen; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid;
palladium on activated charcoal;
In
1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1248/cpb.43.1706