Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars

The protecting-group-free asymmetric synthesis of 1,2,4-trideoxy-1,4-imino-L-xylitol is readily achieved in five steps from 2-deoxy-D-ribose and with an overall yield of 48%. Key in this synthesis is the application of our recently developed Vasella-reductive amination and carbamate annulation metho...

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Detalles Bibliográficos
Autores principales: Dangerfield, Emma Marie, Plunkett, Catherine Heather, Stocker, Bridget Louise, Timmer, Mattie Simon Maria
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6254907/
https://www.ncbi.nlm.nih.gov/pubmed/20032893
http://dx.doi.org/10.3390/molecules14125298
Descripción
Sumario:The protecting-group-free asymmetric synthesis of 1,2,4-trideoxy-1,4-imino-L-xylitol is readily achieved in five steps from 2-deoxy-D-ribose and with an overall yield of 48%. Key in this synthesis is the application of our recently developed Vasella-reductive amination and carbamate annulation methodologies to the synthesis of 2-deoxy-aza-sugars. The carbamate annulation occurred with excellent yield and diastereoselectively (>20:1 d.r.), in favour of the 3,4-cis isomer.

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