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Named reactions

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Sphingosine

Chemical structure of Sphingosine
C18H37NO2
Author Lanny S. Liebeskind
Publication year 2007
Synthesis type Total synthesis
Number of steps 7 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
PhSH, DCC, HOBt
EtOAc
0 °C to RT, 16 h, 89%
Chemical structure
TBSCl, DMAP, N-Methylmorpholine
DMF
0 °C to RT, 30 min, 99%
Chemical structure

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Part 2 of 3
Chemical structure
  1. HBBr2.Me2S
  2. H2O
CH2Cl2
0 °C to RT, 7 h, 77%
Chemical structure

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Part 3 of 3
Chemical structure
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Chemical structure
Pd2(dba)3, CuTC, P(OEt)3
THF
RT, 10 h, 94%

See the Liebeskind-Srogl Coupling
Chemical structure
Li(Ot-Bu)3AlH
EtOH
-78 °C, 2 h, 96%
Chemical structure
HCl
MeOH, H2O
0 °C to RT, 30 min, 99%
Chemical structure
CF3CO2H
CH2Cl2
0 °C to RT, 30 min, 90%
Chemical structure

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