Site-Selective Debenzylation of C-Allyl Iminosugars Enables Their Stereocontroled Structure Diversification at the C-2 Position
| Autor: | Foucart, Quentin, Marrot, Jérôme, Désiré, Jérôme, Blériot, Yves |
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| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Chemistry Stereochemistry Organic Chemistry Structural diversity Regioselectivity 010402 general chemistry 01 natural sciences Biochemistry Reductive elimination 0104 chemical sciences chemistry.chemical_compound Site selective Stereoselectivity Physical and Theoretical Chemistry Derivative (chemistry) |
| Zdroj: | Organic letters. 21(12) |
| ISSN: | 1523-7052 |
| Popis: | A C-2 regioselective debenzylative cycloetherification/reductive elimination sequence applied to perbenzylated C-allyl iminosugars is described. This NIS/TMSOTf-triggered deprotection was successfully applied to five-, six-, and seven-membered C-allyl iminosugars including 1,2 cis and 1,2 trans stereoisomers. It allows rapid introduction of structural diversity at the key C-2 position in a stereoselective manner exploiting the anchimeric assistance of the intracyclic N-benzyl group, giving access to the 2-acetamido and 2-fluoro d-gluco configured C-allyl iminosugars and to the epimeric d-manno derivative. |
| Databáze: | OpenAIRE |
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