Acetonide

Acetonide scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • 2,2-Dimethoxypropane Camphorsulfonic acid
    CH2Cl2
    0 °C - RT
    2 - 7 h
    82-86 %
    intermediate structure
    2,2-Dimethoxypropane, Camphorsulfonic acid
    CH2Cl2
    RT, 7 h, 82%
    intermediate structure
    intermediate structure
    2,2-Dimethoxypropane, Camphorsulfonic acid
    CH2Cl2
    0 °C to RT, 2 h, 86%
    intermediate structure
  • 2,2-Dimethoxypropane Pyr.TsOH
    DMF
    RT
    60 min
    88 %
    intermediate structure
    2,2-Dimethoxypropane, Pyr.TsOH
    DMF
    RT, 60 min, 88%
    intermediate structure
  • 2-Methoxypropene Camphorsulfonic acid
    THF
    RT
    18 h
    95 %
    intermediate structure
    2-Methoxypropene, Camphorsulfonic acid
    THF
    RT, 18 h, 95%
    intermediate structure
  • CuSO4
    Acetone
    RT
    36 h
    83 %
    intermediate structure
    CuSO4
    Acetone
    RT, 36 h, 83%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • HCl
    MeOH H2O
    -12 °C - RT
    5 h - 3d
    65-85 %
    intermediate structure
    HCl
    MeOH, H2O
    RT, 5 h, 80%
    intermediate structure
    intermediate structure
    HCl
    MeOH, H2O
    RT, 3 d, 85%
    intermediate structure
    intermediate structure
    HCl
    MeOH
    -12 to 0 °C, 7 h, 65%
    intermediate structure
  • HCl
    THF H2O
    RT
    5 h
    92 %
    intermediate structure
    HCl
    THF, H2O
    RT, 5 h, 92%
    intermediate structure
  • CF3CO2H
    MeCN H2O
    0 °C - RT
    45 min
    85 %
    intermediate structure
    CF3CO2H
    MeCN, H2O
    0 °C to RT, 45 min, 85%
    intermediate structure