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Síntesis estereoselectiva controlada por reactivo de α-glucanos

Liming Wang¹, Herman S Overkleeft¹, Gijsbert A van der Marel¹

¹Leiden Institute of Chemistry , Leiden University , Einsteinweg 55 , 2333 CC Leiden , The Netherlands.

Journal of the American Chemical Society

|March 20, 2018

Resumen

Los investigadores desarrollaron un método de glucosilación estereoselectiva para construir enlaces cis-glucósidos. Esta estrategia controla la activación del reactivo para pares específicos de donante-aceptor, lo que permite una síntesis eficiente de carbohidratos complejos como el no-sacárido de Mycobacterium tuberculosis.

Área de la Ciencia:

Química de los carbohidratos
Síntesis orgánica
Glicobiología

Sus antecedentes:

La síntesis estereoselectiva de enlaces glucósidos es un desafío debido a las variaciones en las propiedades de donante-aceptor.
El control de los resultados de la glucosilación requiere un ajuste preciso de los reactivos y los grupos de protección.

Objetivo del estudio:

Desarrollar un método general para la síntesis estereoselectiva de enlaces cis-glucósidos.
Demostrar una estrategia adaptable a diferentes nucleófilos de alcohol (primario y secundario).

Principales métodos:

Se utilizó un único tipo de donante de glucosilo (imidato de glucosilo perbenzilado).
Se empleó una estrategia de grupo de protección utilizando únicamente éteres de bencilo.
Se ha activado el donante con combinaciones específicas de reactivos (TMSOTf/DMF para los alcoholes secundarios, TMSI/Ph3PO para los alcoholes primarios).

Principales resultados:

Se ha logrado una instalación totalmente estereoselectiva de enlaces cis-glucósidos.
Actividad diferencial demostrada basada en la reactividad del aceptor y la elección del reactivo.
Se aplicó con éxito el método a la síntesis modular de un no-sacárido de Mycobacterium tuberculosis.

Conclusiones:

La estrategia desarrollada ofrece un control preciso de la estereoselectividad en la glucosilación.
Este método proporciona un enfoque versátil para sintetizar oligosacáridos complejos.
Los hallazgos son significativos para el avance de la síntesis de carbohidratos y la investigación de la glucobiología.

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