Protecting Groups

Alcohol
Protecting GroupProtection ConditionDeprotection condition
1. TMSCl, Py, DCM

2. TMSOTf, Et3N (or) 2.6-Lutidine, DCM		1. HCl, THF, H2O


1. TBDMSCl, Im, DCM (or) DMF

2. TBDMSOTf, 2,6-Lutidine, DCM



1. HCl, THF (or) MeOH, H2O

2. PPTS or CSA, EtOH (or) MeOH

3. BF3.OEt2, DCM

4. TBAF, THF

1. TIPSCl, DMAP, DMF


1. HCl, THF (or) MeOH, H2O

2. TBAF, THF
1. TBDPSCl, Im (or) DMAP, DMF (or) THF (or) DCM
1. TBAF, THF
1. BnBr, K2CO3, acetone

2. BnBr, NaH, TBAI, THF		1. Pd/C, H2, EtOH (or) MeOH (or) EtOAc

2. Pd(OH)2/C, H2, EtOH (or) MeOH
1. PMBCl, NaH, THf (or) DMF

2. PMB trichloroacetamidate, TfOH (cat.), DCM		1. DDQ, buffer (pH 7), DCM
1. Ac2O, DMAP, DCM (or) toluene

2. Ac2O, Py (solvent)

1. LiOH, THF, H2O

2. KOH. MeOH, H2O

3. K2CO3, MeOH
1. BzCl, DMAP (or) Py, DCM

2. BzCl, Py (solvent)		1. KOH. EtOH

2. K2CO3, MeOH, THF
1. MOMCl, DMAP (or) DIPEA, DCM

1. HCl, MeOH, H2O

2. TMSBr, DCM
1. MEMCl, DIPEA, DCM1. ZnBr2, DCM
1. 3,4-Dihydropyran (DHP), PTSA (or) PPTS (cat.), DCM1.. PTSA (or) PPTS, MeOH (or) EtOH

2. AcOH, H2O
1. NaH, MeI, THF1. TMSCl, NaI, CH3CN, H2O

2. TMSI, CH3CN

1,2-Diol
Protecting GroupProtection ConditionDeprotection condition
1. 2,2-Dimethoxypropane, PPTS, DMF

2. 2,2-Dimethoxypropanev, CSA, DCM

3. CuSO4, acetone		1. HCl, THF (or) MeOH, H2O

2. TFA, CH3CN, H2O


1. PhCH(OMe)2, PPTS, Toluene1. Pd(OH)2/C, H2, EtOH
1. CDI, toluene

2. CDI, NaH, THF (or) DMF
1. KOH, MeOH
Amine
Protecting GroupProtection ConditionDeprotection condition
1. Boc2O, Et3N, DCM

2. Boc2O, NaHCO3, EtOAc, H2O
1. TFA, DCM

2. AcCl, EtOH

3. TMSOTf, Et3N, DCM
1. BnCOOCl (CbzCl), Na2CO3, THF

2. BnCOOCl (CbzCl), K2CO3, CH3CN		1. Pd/C (or) Pd(OH)2,, H2, MeOH

2. Pd/C, HCOONH4, MeOH
1. BnBr, K2CO3, MeOH1. Pd/C, H2, HCl, EtOH
1. Ac2O, DMAP, DCM

2. Ac2O, Py (solvent)		1. HCl, MeOH

2. KOH, MeOH, H2O
1. TFAA, Py, DCM1. K2CO3, MeOH, H2O

2. NaOMe, MeOH, DCM
1. ClCOOMe, DMAP, DCM1. HBr, AcOH
1. HCOOEt, Et3N

2. HCOOAc, HCOOH		1. HCl, MeOH, H2O

2. NaOH, MeOH
Aldehyde,
Ketone
Protecting GroupProtection ConditionDeprotection condition
1. CH(OMe)3, PTSA, MeOH1. PPTS, acetone, H2O

1. CH(OEt)3, PTSA, EtOH		1. HCl, THF, H2O
1. (CH2OH)2, PTSA (or) Dowex acidic resin, toluene
1. HCl, MeOH, H2O

2. PTSA (or) PPTS, acetoe, H2O
Carboxylic
acid
Protecting GroupProtection ConditionDeprotection condition
1. BnOH, PTSA, toluene1. Pd/C, H2, MeOH (or) EtOAc
1. Fischer Esterification
(cat. H+, MeOH)		1. LiOH (or) NaOH, THF (or) MeOH, H2O
Phenol
Protecting GroupProtection ConditionDeprotection condition
1. TBDMSCl, Im, DMF1. HCl, THF (or) CH3CN, H2O

1. TIPSCl, Im, DMF		1. TBAF, THF
1. BnBr, K2CO3, CH3CN (or) DMF

2. BnBr, AgO, DCM		1. Pd/C, H2, MeOH

2. HBr, DCM
1. Me2SO4, KOH, MeOH, H2O

2. Me2SO4, K2CO3, acetone

3. MeI, NaOH, TBAB, H2O

4. Me3O+BF4–, proton sponge, DCM
[proton sponge is 1,8-Bis(dimethylamino)naphthalene]		1. BBr3, DCM

2. Pyr.HCl

3. NaSEt, DMF
PG strategies

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