Triethylsilyl ether (TES)

Triethylsilyl ether (TES) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • TESCl
    Pyr
    -78 °C - RT
    30 min - 12 h
    85-92 %
    intermediate structure
    TESCl
    Pyr
    RT, 12 h, 85%
    intermediate structure
    intermediate structure
    TESCl
    Pyr
    RT, 30 min, 87%
    "92 % yield based on 95 % conversion."
    intermediate structure
  • TESCl Imidazole
    DMF
    0 °C
    60 min
    99 %
    intermediate structure
    TESCl, Imidazole
    DMF
    0 °C, 60 min, 99%
    intermediate structure
  • TESCl Imidazole DMAP
    DMF
    0 °C - RT
    16 h
    85 %
    intermediate structure
    TESCl, Imidazole, DMAP
    DMF
    0 °C to RT, 16 h, 85%
    intermediate structure
  • TESOTf 2,6-Lutidine
    CH2Cl2
    0 °C - RT
    30 min
    83-92 %
    intermediate structure
    TESOTf, 2,6-Lutidine
    CH2Cl2
    0 °C, 30 min, 92%
    intermediate structure
    intermediate structure
    TESOTf, 2,6-Lutidine
    CH2Cl2
    RT, 30 min, 83%
    intermediate structure
  • TESOTf Et3N
    CH2Cl2
    -78 °C
    30 min
    92 %
    intermediate structure
    TESOTf, Et3N
    CH2Cl2
    -78 °C, 30 min, 92%
    intermediate structure
  • TESOTf
    Pyr
    -23 °C
    10 min
    98 %
    intermediate structure
    TESOTf
    Pyr
    -23 °C, 10 min, 98%
    intermediate structure
  • TESCl Pyr
    CH2Cl2
    -78 - -20 °C
    10 h
    92 %
    intermediate structure
    TESCl, Pyr
    CH2Cl2
    -78 to -20 °C, 10 h, 92%
    intermediate structure
  • TESOTf i-Pr2NEt
    CH2Cl2
    -60 - 0 °C
    2.5 h
    71 %
    intermediate structure
    TESOTf, i-Pr2NEt
    CH2Cl2
    -60 to 0 °C, 2.5 h, 71%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • Pyr.HF
    THF
    0 °C - RT
    60 min - 72 h
    80-100 %
    intermediate structure
    Pyr.HF
    THF
    RT, 90 min, 80%
    intermediate structure
    intermediate structure
    Pyr.HF
    THF
    RT, 2 h, 88%
    intermediate structure
    intermediate structure
    Pyr.HF
    THF
    RT, 60 min, 96%
    intermediate structure
    intermediate structure
    Pyr.HF
    THF
    RT, 72 h, 100%
    intermediate structure
    intermediate structure
    Pyr.HF
    THF
    0 °C, 4 h, 93%
    intermediate structure
  • Pyr.HF
    MeCN
    0 °C
    11 h
    100 %
    intermediate structure
    Pyr.HF
    MeCN
    0 °C, 11 h, 100%
    intermediate structure
  • n-Bu4N+ F-
    THF
    -78 °C - RT
    2 - 4 h
    72-88 %
    intermediate structure
    n-Bu4N+ F-
    THF
    -78 °C, 4 h, 72%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    -50 °C to RT, 2 h, 88%
    intermediate structure
  • n-Bu4N+ F- AcOH
    THF
    RT
    18 h
    87 %
    intermediate structure
    n-Bu4N+ F-, AcOH
    THF
    RT, 18 h, 87%
    intermediate structure
  • HCl
    THF H2O
    RT
    60 min
    89 %
    intermediate structure
    HCl
    THF, H2O
    RT, 60 min, 89%
    intermediate structure
  • CF3CO2H
    MeCN H2O
    0 °C
    4 h
    93 %
    intermediate structure
    CF3CO2H
    MeCN, H2O
    0 °C, 4 h, 93%
    intermediate structure
  • K2CO3
    MeOH
    0 °C - RT
    13 h
    92 %
    intermediate structure
    K2CO3
    MeOH
    0 °C to RT, 13 h, 92%
    intermediate structure