A Novel Synthetic Approach to C-Glycosyl-d- and l-Alanines

C-Glycosyl-(S)- and (R)-alanines 12a and 12b were synthesized from the known β-C-glycoside 1. The nitrogen function was introduced by aza-Claisen rearrangement of the allylic thiocyanate 7, derived from the corresponding alcohol 6. The absolute configuration of the newly created chiral carbon center...

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Detalles Bibliográficos
Autores principales: Martinková, Miroslava, Gonda, Jozef, Raschmanová, Jana, Novodomská, Alexandra, Kožíšek, Jozef, Perasinová, Lucia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2008
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6244940/
https://www.ncbi.nlm.nih.gov/pubmed/19078857
http://dx.doi.org/10.3390/molecules13123171
Descripción
Sumario:C-Glycosyl-(S)- and (R)-alanines 12a and 12b were synthesized from the known β-C-glycoside 1. The nitrogen function was introduced by aza-Claisen rearrangement of the allylic thiocyanate 7, derived from the corresponding alcohol 6. The absolute configuration of the newly created chiral carbon center (C-3) was assigned by X-ray diffraction analysis of the intermediate 3(S)-isothiocyanato-d-glycero-d-galacto-decose 8a.

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