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Named reactions

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Search synthesis

Oseltamivir

Chemical structure of Oseltamivir
C16H28N2O4
Author Ulrich Zutter
Publication year 2008
Synthesis type Total synthesis
Number of steps 13 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
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Chemical structure
KOt-Bu
DMSO
50 °C, 5 h

See the Williamson Ether Synthesis
Chemical structure
NBS
DMF
0 °C to RT, 19 h, 90% (2 steps)
Chemical structure
CO, Pd(OAc)2, dppp, KOAc
10 atm
EtOH
110 °C, 15 h, 95%
Chemical structure
H2, Ru/Al2O3
100 atm
EtOAc
60 °C, 24 h, 82%
Chemical structure
TMSCl, NaI
MeCN, H2O
40 °C, 15 h, 97%
Chemical structure
Pig liver esterase
Buffer (pH = 8)
35 °C, 46 h, 98%

Selectivity : 98:02 er
Chemical structure
(PhO)2P(O)N3, Et3N
CH2Cl2
40 °C, 16 h, 78%

See the Curtius Rearrangement
Chemical structure
Boc2O, NaH, DMAP
PhMe
RT to Reflux, 5.5 h
Chemical structure
Tf2O, Pyr
CH2Cl2
-10 °C, 3 h, 85% (2 steps)
Chemical structure
NaN3
Acetone, H2O
RT, 15 h, 78%
Chemical structure
H2, Co (Raney)
1 atm
RT, 20 h
Chemical structure
Ac2O, Et3N
EtOAc
RT, 60 min
Chemical structure
HBr
EtOAc, AcOH
RT, 20 h, 83% (3 steps)
Chemical structure

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