Trimethylsilyl ether (TMS)

Trimethylsilyl ether (TMS) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • TMSCl Pyr
    CH2Cl2
    0 °C
    15 min
    96 %
    intermediate structure
    TMSCl, Pyr
    CH2Cl2
    0 °C, 15 min, 96%
    intermediate structure
  • TMSOTf Et3N
    CH2Cl2
    -10 to -5 °C
    60 min
    72 %
    intermediate structure
    TMSOTf, Et3N
    CH2Cl2
    -10 to -5 °C, 60 min, 72%
    intermediate structure
  • TMSOTf 2,6-Lutidine
    CH2Cl2
    RT
    4 h
    100 %
    intermediate structure
    TMSOTf, 2,6-Lutidine
    CH2Cl2
    RT, 4 h, 100%
    intermediate structure
  • TMSCN
    CH2Cl2
    RT
    15 h
    82 %
    intermediate structure
    TMSCN
    CH2Cl2
    RT, 15 h, 82%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • HCl
    THF H2O
    0 °C - RT
    60 min - 6 h
    89-100 %
    intermediate structure
    HCl
    THF, H2O
    RT, 60 min, 89%
    intermediate structure
    intermediate structure
    HCl
    THF
    0 °C, 6 h, 100%
    intermediate structure