Acetate (Ac)

Acetate (Ac) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • Ac2O DMAP
    CH2Cl2
    RT
    30 min - ON
    66-95 %
    intermediate structure
    Ac2O, DMAP
    CH2Cl2
    RT, 2 h, 95%
    intermediate structure
    intermediate structure
    Ac2O, DMAP
    CH2Cl2
    RT, 30 min, 95%
    intermediate structure
    intermediate structure
    Ac2O, DMAP
    CH2Cl2
    RT, 4 h, 94%
    intermediate structure
    intermediate structure
    Ac2O, DMAP
    CH2Cl2
    RT, ON, 89%
    intermediate structure
    intermediate structure
    Ac2O, DMAP
    CH2Cl2
    RT, 30 min, 92%
    intermediate structure
    intermediate structure
    Ac2O, DMAP
    CH2Cl2
    RT, 6 h, 66%
    intermediate structure
  • Ac2O DMAP
    Pyr
    RT
    30 min - 25 h
    66-96 %
    intermediate structure
    Ac2O, DMAP
    Pyr
    RT, 25 h, 72%
    intermediate structure
    intermediate structure
    Ac2O, DMAP
    Pyr
    RT, 16 h, 66%
    intermediate structure
    intermediate structure
    Ac2O, DMAP
    Pyr
    RT, 16 h, 76%
    intermediate structure
    intermediate structure
    Ac2O, DMAP
    Pyr
    RT, 90 min, 87%
    intermediate structure
    intermediate structure
    Ac2O, DMAP
    Pyr
    RT, 13 h, 91%
    intermediate structure
    intermediate structure
    Ac2O, DMAP
    Pyr
    RT, 30 min, 96%
    intermediate structure
  • Ac2O Et3N DMAP
    CH2Cl2
    0 °C - RT
    30 min - 20 h
    76-99 %
    intermediate structure
    Ac2O, DMAP
    CH2Cl2, Et3N
    RT, 60 min, 80%
    intermediate structure
    intermediate structure
    Ac2O, DMAP
    CH2Cl2, Et3N
    RT, 60 min, 97%
    intermediate structure
    intermediate structure
    Ac2O, Et3N, DMAP
    CH2Cl2
    0 °C to RT, 30 min, 99%
    intermediate structure
    intermediate structure
    Ac2O, Et3N, DMAP
    CH2Cl2
    RT, 20 h, 95%
    intermediate structure
    intermediate structure
    Ac2O, Et3N, DMAP
    CH2Cl2
    RT, 4 h, 76%
    intermediate structure
  • Ac2O DMAP
    PhH
    0 - 35 °C
    10 h
    84 %
    intermediate structure
    Ac2O, DMAP
    PhH
    0 to 35 °C, 10 h, 84%
    intermediate structure
  • Ac2O
    Pyr
    RT - Reflux
    15 min - 12 h
    73-100 %
    intermediate structure
    Ac2O
    Pyr
    RT, 15 min, 100%
    intermediate structure
    intermediate structure
    Ac2O
    Pyr
    80-90 °C, 2 h, 92%
    intermediate structure
    intermediate structure
    Ac2O
    Pyr
    RT, 12 h, 96%
    intermediate structure
    intermediate structure
    Ac2O
    Pyr
    60 °C, 3 h, 92%
    intermediate structure
    intermediate structure
    Ac2O
    Pyr
    RT, 3 h, 73%
    intermediate structure
    intermediate structure
    Ac2O
    Pyr
    Reflux, 2 h, 92%
    intermediate structure
    intermediate structure
    Ac2O
    Pyr
    RT, ON, 98%
    intermediate structure
  • I2
    Ac2O
    RT
    10 min
    92 %
    intermediate structure
    Ac2O, I2
    RT, 10 min, 92%
    intermediate structure
  • Sc(OTf)3
    Ac2O
    0 °C
    2 h
    98 %
    intermediate structure
    Sc(OTf)3
    Ac2O
    0 °C, 2 h, 98%
    intermediate structure
  • BF3.OEt2
    AcOH
    50 °C
    18 h
    96 %
    intermediate structure
    BF3.OEt2
    AcOH
    50 °C, 18 h, 96%
    intermediate structure
  • Ac2O Pyr
    CH2Cl2
    RT
    24 h
    92 %
    intermediate structure
    Ac2O, Pyr
    CH2Cl2
    RT, 24 h, 92%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • K2CO3
    MeOH
    0 °C - RT
    15 min - 4 h
    82-100 %
    intermediate structure
    K2CO3
    MeOH
    RT, 15 min, 100%
    intermediate structure
    intermediate structure
    K2CO3
    MeOH
    RT, 4 h, 82%
    intermediate structure
    intermediate structure
    K2CO3
    MeOH
    0 °C, 15 min, 95%
    intermediate structure
    intermediate structure
    K2CO3
    MeOH
    RT, 30 min, 82%
    intermediate structure
  • KOH
    MeOH H2O
    Reflux
    2 h
    85-100 %
    intermediate structure
    KOH
    MeOH, H2O
    Reflux, 2 h, 100%
    intermediate structure
    intermediate structure
    KOH
    MeOH, H2O
    Reflux, 2 h, 85%
    intermediate structure
  • LiOH
    THF H2O
    RT
    60 min
    92 %
    intermediate structure
    LiOH
    THF, H2O
    RT, 60 min, 92%
    intermediate structure
  • NH3
    MeOH
    0 °C
    30 min
    90 %
    intermediate structure
    NH3
    MeOH
    0 °C, 30 min, 90%
    intermediate structure
  • HCl
    H2O
    RT
    2 h
    80 %
    intermediate structure
    HCl
    H2O
    RT, 2 h, 80%
    intermediate structure
  • NaOEt
    EtOH
    4 °C - RT
    10 h
    70 %
    intermediate structure
    NaOEt
    EtOH
    4 °C to RT, 10 h, 70%
    intermediate structure
  • KOH
    EtOH
    RT
    20 min
    80 %
    intermediate structure
    KOH
    EtOH
    RT, 20 min, 80%
    intermediate structure