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1. Site-Selective Debenzylation of C-Allyl Iminosugars Enables Their Stereocontroled Structure Diversification at the C-2 Position

Author

Foucart, Quentin, Marrot, Jérôme, Désiré, Jérôme, and Blériot, Yves

Subjects
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)
Abstract

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.

Published
2019

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