Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigatorTohru Fukuyama
Publication year2007
Synthesis typeTotal
Number of steps 14 (linear)
References
Part 1 of 1
intermediate structure
ClCO2Bn, NaBH4
MeOH
-47 to 0 °C, 50 min
intermediate structure
Acrolein
MeCN, H2O
RT, 14 h
intermediate structure
NaClO2, NaH2PO4, 2-Methyl-2-butene
t-BuOH, H2O
0 °C to RT, 70 min
intermediate structure
Br2, NaHCO3
CH2Cl2, H2O
RT, , 26% (4 steps)
intermediate structure
H2, Pd/C, Boc2O
EtOH, THF
RT, 2 h, 92%
intermediate structure
RuO2, NaIO4
DCE, H2O
80 °C, 3.5 h, 86%
intermediate structure
NH3
t-BuOH, THF
0 °C, 2.5 h, 95%
intermediate structure
MsCl, Et3N
CH2Cl2
RT, 40 min, 91%
intermediate structure
AllylOH, PhI(OAc)2
DCE
60 °C, 11 h, 88%
intermediate structure
NaOEt
EtOH
0 °C, , 87%
intermediate structure
3-Pentanol, BF3.OEt2
-20 °C, 50 min, 62%
intermediate structure
CF3CO2H
CH2Cl2
0 °C to RT, 3 h
intermediate structure
Ac2O
Pyr
RT, 60 min, 72% (2 steps)
intermediate structure
Pd/C, Ph3P, Dimethylbarbituric acid
EtOH
Reflux, 60 min, 76%
intermediate structure