tert-Butyldimethylsilyl ether (TBS, TBDMS)

tert-Butyldimethylsilyl ether (TBS, TBDMS) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • TBSCl Imidazole
    CH2Cl2
    RT
    5 min - 18 h
    88-98 %
    intermediate structure
    TBSCl, Imidazole
    CH2Cl2
    RT, 18 h, 97%
    intermediate structure
    intermediate structure
    TBSCl, Imidazole
    CH2Cl2
    RT, 6 h, 90%
    intermediate structure
    intermediate structure
    TBSCl, Imidazole
    CH2Cl2
    RT, 5 h, 88%
    intermediate structure
    intermediate structure
    TBSCl, Imidazole
    CH2Cl2
    RT, 5 min, 98%
    intermediate structure
  • TBSCl Imidazole
    CH2Cl2 DMF
    RT
    20 min
    99 %
    intermediate structure
    TBSCl, Imidazole
    CH2Cl2, DMF
    RT, 20 min, 99%
    intermediate structure
  • TBSCl Imidazole
    DMF
    0 °C - RT
    6 h - 5 d
    82-98 %
    intermediate structure
    TBSCl, Imidazole
    DMF
    0 °C, 6 h, 82%
    intermediate structure
    intermediate structure
    TBSCl, Imidazole
    DMF
    RT, ON, 98%
    intermediate structure
    intermediate structure
    TBSCl, Imidazole
    DMF
    RT, 5 d, 82%
    intermediate structure
  • TBSCl Imidazole DMAP
    CH2Cl2
    0 °C - RT
    60 min - ON
    89-95 %
    intermediate structure
    TBSCl, Imidazole, DMAP
    CH2Cl2
    RT, ON, 89%
    intermediate structure
    intermediate structure
    TBSCl, Imidazole, DMAP
    CH2Cl2
    0 °C, 60 min, 95%
    intermediate structure
  • TBSCl i-Pr2NEt DMAP
    CH2Cl2
    0 °C - RT
    3 h
    88 %
    intermediate structure
    TBSCl, i-Pr2NEt, DMAP
    CH2Cl2
    0 °C to RT, 3 h, 88%
    "The following protection / deprotection sequence was due to a late deviation from the initial plan."
    intermediate structure
  • TBSCl
    CH2Cl2
    RT
    60 min
    100 %
    intermediate structure
    TBSCl
    CH2Cl2
    RT, 60 min, 100%
    intermediate structure
  • TBSOTf 2,6-Lutidine
    CH2Cl2
    0 °C
    15 - 60 min
    90-100 %
    intermediate structure
    TBSOTf, 2,6-Lutidine
    CH2Cl2
    0 °C, 60 min, 100%
    intermediate structure
    intermediate structure
    TBSOTf, 2,6-Lutidine
    CH2Cl2
    0 °C, 15 min, 90%
    intermediate structure
    intermediate structure
    TBSOTf, 2,6-Lutidine
    CH2Cl2
    0 °C, 40 min, 96%
    intermediate structure
  • TBSOTf 2,6-Lutidine DMAP
    CH2Cl2
    0 °C
    4 h
    95 %
    intermediate structure
    TBSOTf, 2,6-Lutidine, DMAP
    CH2Cl2
    0 °C, 4 h, 95%
    intermediate structure
  • TBSOTf 2,6-Lutidine
    MeCN
    RT
    60 min
    89 %
    intermediate structure
    TBSOTf, 2,6-Lutidine
    MeCN
    RT, 60 min, 89%
    intermediate structure
  • TBSCl Et3N DMAP
    DMF
    -20 °C - RT
    2.5 - 3 h
    69-71 %
    intermediate structure
    TBSCl, Et3N, DMAP
    DMF
    -20 to -5 °C, 2.5 h, 69%
    intermediate structure
    intermediate structure
    TBSCl, Et3N, DMAP
    DMF
    RT, 3 h, 71%
    intermediate structure
  • TBSCl DMAP
    Pyr
    RT
    24 h
    71 %
    intermediate structure
    TBSCl, DMAP
    Pyr
    RT, 24 h, 71%
    intermediate structure
  • TBSCl DMAP N-Methylmorpholine
    DMF
    0 °C - RT
    30 min
    99 %
    intermediate structure
    TBSCl, DMAP, N-Methylmorpholine
    DMF
    0 °C to RT, 30 min, 99%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • n-Bu4N+ F-
    THF
    0 - 70 °C
    15 min - 16 h
    70-100 %
    intermediate structure
    n-Bu4N+ F-
    THF
    RT, 105 min, 85%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    0 °C, 15 min, 99%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    50 °C, 16 h, 95%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    RT, 7 h, 80%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    RT, 8 h, 92%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    50 °C, 60 min, 100%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    70 °C, 4 h, 70%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    RT, 3 h, 99%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    0 °C, 3 h, 100%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    0 °C to RT, 5 h, 97%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    RT, ON, 83%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    0 °C to RT, 3 h, 87%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    RT, 4 h, 93%
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    RT, 60 min, 95%
    "The product is also obtained by the degradation of natural azadirachtin."
    intermediate structure
    intermediate structure
    n-Bu4N+ F-
    THF
    RT, 15 h, 97%
    intermediate structure
  • TASF
    THF
    RT
    15 min - 48 h
    80-94 %
    intermediate structure
    TASF
    THF
    RT, 15 min, 94%
    intermediate structure
    intermediate structure
    TASF
    THF
    RT, 48 h, 80%
    intermediate structure
  • HCl
    THF H2O
    0 °C - RT
    30 min - 6 h
    83-100 %
    intermediate structure
    HCl
    THF, H2O
    RT, 6 h, 95%
    intermediate structure
    intermediate structure
    HCl
    THF, H2O
    0 °C, 60 min, 83%
    intermediate structure
    intermediate structure
    HCl
    THF, H2O
    RT, 3 h, 99%
    intermediate structure
    intermediate structure
    HCl
    THF, H2O
    RT, 60 min, 100%
    intermediate structure
    intermediate structure
    HCl
    THF, H2O
    RT, 3 h, 96%
    intermediate structure
    intermediate structure
    HCl
    THF, H2O
    RT, 30 min, 88%
    intermediate structure
  • HCl
    MeOH H2O
    0 °C - RT
    30 min - ON
    83-99 %
    intermediate structure
    HCl
    MeOH, H2O
    RT, 3 h, 89%
    intermediate structure
    intermediate structure
    HCl
    MeOH, H2O
    RT, ON, 83%
    intermediate structure
    intermediate structure
    HCl
    MeOH, H2O
    0 °C to RT, 30 min, 99%
    intermediate structure
  • Camphorsulfonic acid
    MeOH
    RT
    60 min
    90 %
    intermediate structure
    Camphorsulfonic acid
    MeOH
    RT, 60 min, 90%
    intermediate structure
  • Camphorsulfonic acid
    MeOH CH2Cl2
    RT
    30 min
    97 %
    intermediate structure
    Camphorsulfonic acid
    MeOH, CH2Cl2
    RT, 30 min, 97%
    intermediate structure
  • Pyr.TsOH
    EtOH
    RT
    ON
    93 %
    intermediate structure
    Pyr.TsOH
    EtOH
    RT, ON, 93%
    intermediate structure
  • BF3.OEt2
    CH2Cl2
    RT
    14 h
    89 %
    intermediate structure
    BF3.OEt2
    CH2Cl2
    RT, 14 h, 89%
    intermediate structure
  • Pyr.HF
    THF
    RT
    15 min - 3 h
    76-91 %
    intermediate structure
    Pyr.HF
    THF
    RT, 3 h, 91%
    intermediate structure
    intermediate structure
    Pyr.HF
    THF
    RT, 15 min, 76%
    intermediate structure
  • AcOH
    H2O
    RT
    60 min
    100 %
    intermediate structure
    AcOH
    H2O
    RT, 60 min, 100%
    intermediate structure
  • LiBF4
    MeCN H2O
    45-50 °C
    31 h
    98 %
    intermediate structure
    LiBF4
    MeCN, H2O
    45-50 °C, 31 h, 98%
    intermediate structure
  • Pyr.HF
    MeCN H2O
    RT - 35 °C
    34 h
    85 %
    intermediate structure
    Pyr.HF
    MeCN, H2O
    RT to 35 °C, 34 h, 85%
    intermediate structure
  • KF.2H2O Et3NBn+ Cl-
    MeCN
    60 °C
    10 h
    84 %
    intermediate structure
    KF.2H2O, Et3NBn+ Cl-
    MeCN
    60 °C, 10 h, 84%
    intermediate structure