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Total Synthesis of Tri‐, Hexa‐ and Heptasaccharidic Substructures of the O‐Polysaccharide of Providencia rustigianii O34

A general and efficient strategy for synthesis of tri‐, hexa‐ and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α‐linked galactosam...

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Detalles Bibliográficos
Autores principales: Ahadi, Somayeh, Awan, Shahid I., Werz, Daniel B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7318715/
https://www.ncbi.nlm.nih.gov/pubmed/32092205
http://dx.doi.org/10.1002/chem.202000496
Descripción
Sumario:A general and efficient strategy for synthesis of tri‐, hexa‐ and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α‐linked galactosamine and the two embedded α‐fucose units, which are either branched at positions‐3 and ‐4 or further linked at their 2‐position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.