tert-Butyldiphenylsilyl ether (TBDPS)

tert-Butyldiphenylsilyl ether (TBDPS) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • TBDPSCl Imidazole
    DMF
    0 °C - RT
    60 min - ON
    90-95 %
    intermediate structure
    TBDPSCl, Imidazole
    DMF
    RT, 60 min, 95%
    intermediate structure
    intermediate structure
    TBDPSCl, Imidazole
    DMF
    0 °C to RT, ON, 90%
    intermediate structure
    intermediate structure
    TBDPSCl, Imidazole
    DMF
    RT, 6 h, 92%
    intermediate structure
  • TBDPSCl Imidazole
    THF
    0 °C - RT
    18 - 52 h
    82-92 %
    intermediate structure
    TBDPSCl, Imidazole
    THF
    0 °C to RT, 52 h, 82%
    intermediate structure
    intermediate structure
    TBDPSCl, Imidazole
    THF
    RT, 18 h, 92%
    intermediate structure
  • TBDPSCl Imidazole DMAP
    CH2Cl2
    RT
    12 h
    85 %
    intermediate structure
    TBDPSCl, Imidazole, DMAP
    CH2Cl2
    RT, 12 h, 85%
    intermediate structure
  • TBDPSCl DMAP
    CH2Cl2
    RT
    2 h
    98 %
    intermediate structure
    TBDPSCl, DMAP
    CH2Cl2
    RT, 2 h, 98%
    intermediate structure
  • TBDPSCl Et3N DMAP
    CH2Cl2
    0 °C - RT
    4 h
    96 %
    intermediate structure
    TBDPSCl, Et3N, DMAP
    CH2Cl2
    0 °C to RT, 4 h, 96%
    intermediate structure
  • TBDPSCl Imidazole
    CH2Cl2
    RT
    30 min
    100 %
    intermediate structure
    TBDPSCl, Imidazole
    CH2Cl2
    RT, 30 min, 100%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • n-Bu4N+ F-
    THF
    0 - 70 °C
    15 min - 7 h
    80-97 %
    intermediate structure
    n-Bu4N+ F-
    THF
    70 °C, 2 h, 95%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    0 °C to RT, 70 min, 92%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    RT, 4 h, 97%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    0 °C, 15 min, 85%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    RT, 7 h, 80%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    0 °C to RT, 4 h, 94%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    0 °C to RT, 90 min, 95%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    0 °C to RT, 3 h, 87%
    intermediate structure
  • TASF
    CH2Cl2
    0 °C to RT
    60 min
    95 %
    intermediate structure
    TASF
    CH2Cl2
    0 °C to RT, 60 min, 95%
    intermediate structure
  • HF
    MeCN H2O
    RT
    60 min
    95 %
    intermediate structure
    HF
    MeCN, H2O
    RT, 60 min, 95%
    intermediate structure