Synthesis of Sphingosine

Structure of Sphingosine

C18H37NO2

Principal investigatorLanny S. Liebeskind
Publication year2007
Synthesis typeTotal
Number of steps 7 (3 parts)
References
Org. Lett. 2007, 9, 2993.
Part 1 of 3
intermediate structure
DCC, HOBt, PhSH
EtOAc
0 °C to RT, 16 h, 89%
intermediate structure
DMAP, TBSCl, N-Methylmorpholine
DMF
0 °C to RT, 30 min, 99%
intermediate structure
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Part 2 of 3
intermediate structure
  1. HBBr2.Me2S
  2. H2O
CH2Cl2
0 °C to RT, 7 h, 77%
intermediate structure
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Part 3 of 3
intermediate structure + intermediate structure
Pd2(dba)3, P(OEt)3, CuTC
THF
RT, 10 h, 94%
See the Liebeskind-Srogl Coupling
intermediate structure
Li(Ot-Bu)3AlH
EtOH
-78 °C, 2 h, 96%
intermediate structure
HCl
H2O, MeOH
0 °C to RT, 30 min, 99%
intermediate structure
CF3CO2H
CH2Cl2
0 °C to RT, 30 min, 90%
intermediate structure
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