Glycosamine Derivatives through Metal‐Catalyzed C−N Bond Formation on Protected and Unprotected 2‐Iodoglycals

Glycosamines are important building blocks of natural biopolymers. The development of synthetic routes to such glycoside family is of big interest in terms of biological application. Herein, access to glycosamine derivatives through dual nickel/copper‐catalyzed C−N bond formation via a cross‐couplin...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-03, Vol.2021 (10), p.1521-1524
Main Authors: Malinowski, Maciej, Banoun, Camille, Robichon, Morgane, Lubin‐Germain, Nadège, Ferry, Angélique
Format: Article
Language:English
Subjects:
2-Iodoglycals
Biopolymers
Bonding
Carbohydrates
Chemical Sciences
Cross coupling
Homogeneous catalysis
Hydrogenolysis
Protecting group-free
Synthesis
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Summary:Glycosamines are important building blocks of natural biopolymers. The development of synthetic routes to such glycoside family is of big interest in terms of biological application. Herein, access to glycosamine derivatives through dual nickel/copper‐catalyzed C−N bond formation via a cross‐coupling reaction is presented. Diverse benzyl‐ and cyclic amide‐containing glycals were successfully synthesized in moderate to excellent yields starting from perbenzylated and protecting group‐free 2‐iodoglycals. 16 examples presenting d‐glucal or d‐galactal configuration and an electron‐rich or electron‐poor amide moiety in position 2 of the carbohydrate are obtained by this methodology. Post‐functionalization by hydrogenolysis conditions of three synthesized compounds allows access to d‐mannosamine and d‐talosamine mimics. Dual nickel/copper‐catalyzed C−N bond formation on perbenzylated and protecting group‐free 2‐iodoglycals was developed as straightforward access to glycosamine analogs. Diverse cyclic‐ and benzyl amides were successfully introduced in position 2 of glycal scaffolds. Post‐functionalization by hydrogenolysis of these compounds let to reach mannosamine‐ and talosamine‐type derivatives.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202001618