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1.
Bioorg Med Chem Lett ; 40: 127961, 2021 05 15.
Artigo em Inglês | MEDLINE | ID: mdl-33741461

RESUMO

An efficient method for the synthesis of substituted 5-(hydroxymethyl)piperazin-2-ones was established by using an automated synthesis process. Thirteen piperazinones were synthesized from chiral α-bromocarboxylic acids and Garner's aldehyde which were prepared by using our originally developed automated synthesizer, ChemKonzert®. The automated method of synthesizing chiral α-bromocarboxylic acids was efficient and safe because the rate of the dropwise addition of the reagent can be controlled using the automated synthesizer. This method is expected to contribute to the synthesis of pharmaceuticals.


Assuntos
Aldeídos/química , Aminoácidos/química , Piperazinas/síntese química , Ciclização , Estrutura Molecular , Oxirredução , Estereoisomerismo
2.
Beilstein J Org Chem ; 13: 106-110, 2017.
Artigo em Inglês | MEDLINE | ID: mdl-28228851

RESUMO

A solution-phase automated synthesis of the versatile synthetic intermediate, Garner's aldehyde, was demonstrated. tert-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer, ChemKonzert. The developed procedure was also useful for the synthesis of Garner's aldehyde analogues possessing fluorenylmethyloxycarbonyl (Fmoc) or benzyloxycarbonyl (Cbz) protection.

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