Synthesis of Dideoxy-octonic Acid and Cyclic and Acyclic Derivatives Thereof.

Czaschke, Christian; de Abreu, Ruben Figueira; Stark, Christian B W; Thiem, Joachim

Czaschke, Christian; de Abreu, Ruben Figueira; Stark, Christian B W; Thiem, Joachim.

Afiliación

Czaschke C; Department of Chemistry, Institute for Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany.
de Abreu RF; Department of Chemistry, Institute for Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany.
Stark CBW; Department of Chemistry, Institute for Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany.
Thiem J; Department of Chemistry, Institute for Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany.

Org Lett ; 22(9): 3373-3376, 2020 05 01.

Article en En | MEDLINE | ID: mdl-32281381

RESUMEN

Oxidative cleavage of N-acetyl-neuraminic acid (Neu5Ac, 1) leads to the open chain octonic acid (ADOA, 2), which under various conditions is transformed into an acyclic acid or ester or into a six- or five-membered octonic acid lactone and lactam, respectively. All reactions proceed with high selectivity and in good yields. Strikingly, a simple switch of reaction conditions from basic to acidic catalysis leads to a complete switch in regioselectivity during a crucial cyclization step.

Asunto(s)

Ácido N-Acetilneuramínico; Catálisis; Ciclización

Texto completo

Añadir a Mi BVS

Imprimir

XML

PubMed Links

Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ácido N-Acetilneuramínico Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Alemania Pais de publicación: Estados Unidos

Texto completo

Añadir a Mi BVS

Imprimir

XML

PubMed Links

Buscar en Google