Dzubeck V,
Schneider JP.
*
University of Delaware, Newark, USA
One-Pot Conversion of Benzyl Carbamates into Fluorenylmethyl Carbamates.
Tetrahedron Lett. 2000;
41: 9953-9956
Key words
benzyl carbamates - fluorenylmethyl carbamates - hydrogenation - protecting groups - solid-phase synthesis
Significance
Since the development of solid-phase peptide synthesis, the 9-fluorenylmethoxycarbonyl (Fmoc) group has been the protecting group of choice for obtaining peptides in high purities. Consequently, the peptide-chemistry industry has been searching for new methods to synthesize Fmoc-protected amino acids and peptides. In 2000, Schneider and Dzubeck developed a simple one-pot protocol for the conversion of N-benzyloxycarbonyl (CBz)-protected amino acid esters or peptides into the corresponding N-Fmoc-protected compounds.
Comment
Conversion of N-Cbz-protected amino acid esters or peptides into the corresponding N-Fmoc-protected derivatives proceeds smoothly through hydrogenation in the presence of Pd/C and 2,2′-bipyridine as a catalyst system in the presence of Fmoc-O-succinimide (Fmoc-OSu). The reaction gives the desired compounds in high yields with excellent stereoselectivities, and it tolerates various other functional groups.
