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Amine:

 

9-Fluorenylmethyl Carbamate (Fmoc)

Fmoc has very good stability in acidic condition, and reasonable stability in inorganic base. It could be removed in a couple minutes with piperidine. You can see a very bright blue spot on your TLC solvent front line.
 

t-Butyl Carbamate  (Boc)

Boc is used extensively in amine protection. It is stable under base condition, could be easily get rid of under TFA/CH2Cl2 (1/1). Boc could be reduced to methyl group under LAH to make single methyl substitution.
 

Benzyl Carbamate (Cbz or Z)

Cbz is another popular carbamate used in the amine protection. It could be easily deprotected under hydrogenation or triethyl silane.
 

Formadide

 
 

N-Phthalimide

Gabriel Amine synthesis is similar to this protection, go figure out the rest of the mechanism.
 

N-2,5-Dimethylpyrrole

Dimethyl Pyrrole protection is very useful in primary amine protection, especially you could not have active proton in your molecule.
 

N-Benzylamine

 
 

N-Triphenylmethylamine

 
 

Demethylation form amine

Very beautiful deprotection method.

Alcohol:

  Methyl protection is easy to put on , but difficult to get rid of.
  Iressa, a cancer drug from AstrazZeneca, was made from this demethylation
  Selective demethylation was done by using ethyl thiol (very stink) and AlCl3.
  MOM, MTM
  BOM
  t-Bu

Lab rat's protection and deprotection procedure:


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