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Named reactions

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Search synthesis

Oseltamivir

Chemical structure of Oseltamivir
C16H28N2O4
Author Masakatsu Shibasaki
Publication year 2007
Synthesis type Total synthesis
Number of steps 14 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
Reagent structure
TMSN3, Y(Oi-Pr)3, 2,6-Dimethylphenol
EtCN
RT, 12 h, 94%

Selectivity : 95:05 er
Cristallized to >99:01 er (72 % yield).
Chemical structure
Boc2O, NaOH, DMAP
MeCN, H2O
RT, 2 h, 98%
Chemical structure
I2, KI, K2CO3
CHCl3
60 °C, 14 h
Chemical structure
DBU
CHCl3
4 °C to RT, 4 h, 85% (2 steps)
Chemical structure
Boc2O, Et3N, DMAP
CH2Cl2
4 °C to RT, 2 h, 99%
Chemical structure
AcSH, 2,6-Lutidine
CHCl3
60 °C, 19 h, 83%
Chemical structure
Cs2CO3
n-BuOH
RT, 16 h, 86%
Chemical structure
Dess-Martin Periodinane
CH2Cl2
4 °C to RT, 25 min, 90%

See the Dess-Martin Oxidation
Chemical structure
(EtO)2P(O)CN, LiCN
THF
-20 °C, 7 h
Chemical structure
Sealed tube
PhMe
140 °C, 40 min, 78% (2 steps)
Chemical structure
  1. p-NO2BzOH, Ph3P, DEAD
  2. LiOH, H2O
THF
-20 °C, 3 h, 80%

See the Mitsunobu Reaction
Chemical structure
Ph3P, DEAD
THF
-20 °C, 75 min, 66%

See the Mitsunobu Reaction
Chemical structure
3-Pentanol, BF3.OEt2
5 Å MS
-20 °C, 75 min, 56%
Chemical structure
HCl
EtOH, H2O
RT, 31.5 h, 60%

See the Pinner Reaction
Chemical structure

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