6533b86ffe1ef96bd12cdc17

RESEARCH PRODUCT

Der (2-Phenyl-2-trimethylsilyl)ethyl-(PTMSE)-Ester – eine neutral spaltbare Carboxyschutzgruppe/The (2-Phenyl-2-trimethylsiylyl)ethyl (PTMSE) Ester – a Carboxy Protecting Group Cleavable under Neutral Conditions

Horst KunzMichael Wagner

subject

chemistry.chemical_classificationChemistrychemistry.chemical_elementPeptideGeneral ChemistryCondensation reactionCleavage (embryo)Tetrabutylammonium fluorideMedicinal chemistrychemistry.chemical_compound(2-Phenyl-2-trimethylsilyl)ethylProtecting groupPalladiumDichloromethane

description

(2-Phenyl-2-trimethylsilyl)ethyl (PTMSE) esters of aminoacids and peptides are stable under the conditions of hydrogenolytic cleavage of benzoxycarbonyl(Z) and benzyl ester groups, base-induced removal of Fmoc groups, palladium(0)-catalyzed removal of allyloxycarbonyl (Aloc) and even acidolytic cleavage of Boc groups. PTMSE esters are also stable under the conditions of peptide condensation reactions. The PTMSE ester is selectively cleaved by treatment with tetrabutylammonium fluoride (TBAF) trihydrate in dichloromethane, i. e. under almost neutral conditions, within a few minutes and, therefore, considered a valuable novel carboxy protecting group.

yearjournalcountryeditionlanguage
2002-08-01Zeitschrift für Naturforschung B
https://doi.org/10.1515/znb-2002-0814