Triisopropylsilyl ether (TIPS)

Triisopropylsilyl ether (TIPS) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • TIPSCl DMAP
    DMF
    RT
    16 h
    100 %
    intermediate structure
    TIPSCl, DMAP
    DMF
    RT, 16 h, 100%
    intermediate structure
  • TIPSCl DMAP
    Et3N
    RT
    25 h
    95 %
    intermediate structure
    TIPSCl, DMAP
    Et3N
    RT, 25 h, 95%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • n-Bu4N+ F-
    THF
    -30 °C - RT
    30 min - 4 h
    84-95 %
    intermediate structure
    n-Bu4N+ F-
    THF
    -30 °C to RT, 4 h, 95%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    RT, 30 min, 84%
    intermediate structure
  • HF
    MeCN
    RT
    2 h
    91 %
    intermediate structure
    HF
    MeCN
    RT, 2 h, 91%
    intermediate structure
  • TASF
    THF
    0 °C
    5 min
    96 %
    intermediate structure
    TASF
    THF
    0 °C, 5 min, 96%
    intermediate structure
  • HCl
    MeOH H2O
    RT
    15 h
    81 %
    intermediate structure
    HCl
    MeOH, H2O
    RT, 15 h, 81%
    intermediate structure
  • Et3N.3HF
    THF
    RT
    2.5 d
    100 %
    intermediate structure
    Et3N.3HF
    THF
    RT, 2.5 d, 100%
    intermediate structure