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RESEARCH PRODUCT
ChemInform Abstract: O-Boronato- and o-Trifluoroborato-Phosphonium Salts Supported by L-α-Amino Acid Side Chain.
Stephen J. ArchibaldGonçalo S. ClementeSylvain JugéJulie BernardBenjamin P. BurkeRaluca Malacea-kabbaraMarie-joëlle Eyminsubject
chemistry.chemical_classificationchemistry.chemical_compoundHydrolysisDipeptideAmino esterschemistryCarboxylic acidAspartic acidSide chainGeneral MedicinePhosphoniumMedicinal chemistryAmino aciddescription
The synthesis of o-boronato- and o-trifluoroborato–phosphonium salts supported by the l-amino acid side chain is described. The synthesis of these new class of amino acid derivatives was achieved by stereoselective quaternization of o-(pinacolato)boronatophenylphosphine with β- or γ-iodo amino acid derivatives which are prepared from l-serine or l-aspartic acid, respectively. The quaternization of the phosphine was performed using either iodo amino ester or carboxylic acid derivatives. In addition, free carboxylic acid and amine derivatives were obtained by saponification or HCl acidolysis of o-boronato–phosphonium amino esters, respectively. The usefulness of these compounds in peptide coupling was demonstrated by coupling an o-boronato–phosphonium amino ester with an aspartic acid moiety. When the o-boronato–phosphonium amino acid or dipeptide derivatives were mixed with fluoride, the corresponding o-trifluoroborated products were cleanly and rapidly obtained in high isolated yields. The hydrolysis of t...
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-08-20 | ChemInform |