Protected Amino Acids / Alfa Chemistry
Introduction To PMB
Introduction To PMB
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Introduction To PMB

p-Methoxybenzyl (PMB) is one of the most stable amino protecting groups. It is stable to most reactions. For example, benzyl (Bn) can be removed under H2/Pd(OH)2 conditions, while PMB remains unchanged.

Introduction of PMB

PMB is generally introduced by reacting PMB-Br or PMB-Cl with a base (K2CO3, i-Pr2NEt, NaH and DBU, etc.) in an organic solvent (such as DMF, DCM and acetonitrile, etc.). It can also be introduced by reductive amination with MeC6H4CHO/NaBH3CN or NaBH(OAc)3.

Removal of PMB

There are many methods for removing PMB. In addition to conventional catalytic hydrogenolysis, oxidative deprotection by ceric ammonium nitrate (CAN), 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or SmI2 and heating in trifluoroacetic acid (TFA) are also often used.