Catalytic Cleavage of the 9-Fluorenylmethoxycarbonyl (Fmoc) Protecting Group under Neat Conditions.

Autor: Traboni S; Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126 Naples, Italy., Esposito F; Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126 Naples, Italy., Ziaco M; Institute of Bio-Molecular Chemistry, National Research Council, Via Campi Flegrei 34, 80078 Pozzuoli, Italy., De Cesare N; Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126 Naples, Italy., Bedini E; Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126 Naples, Italy., Iadonisi A; Department of Chemical Sciences, University of Naples Federico II, via Cinthia 4, 80126 Naples, Italy.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Apr 19; Vol. 26 (15), pp. 3284-3288. Date of Electronic Publication: 2024 Mar 28.
DOI: 10.1021/acs.orglett.4c00918
Abstrakt: This work reports the first solvent-free catalytic approach for the cleavage of the fluorenylmethoxycarbonyl (Fmoc) protecting group from amine and alcohol functionalities. Various saccharide, peptide, and glyco-amino acid substrates were efficiently deprotected by simple treatment with 20 mol % neat 4-dimethylaminopyridine (DMAP) (one of the effective base catalysts found), without any solvent or stoichiometric additives. Small model structures were finally assembled through one-pot, base-catalyzed, solvent-free multistep sequences combining the Fmoc cleavage with esterification, amidation, and/or glycosylation steps.
Databáze: MEDLINE