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Synthesis of N ‐Glycosyl Conjugates through a Multicomponent Domino Process
Author(s) -
Bellucci Maria Cristina,
Volonterio Alessandro
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301887
Subject(s) - chemistry , domino , glycosyl , regioselectivity , conjugate , combinatorial chemistry , organic chemistry , catalysis , mathematical analysis , mathematics
The development of efficient methods for the combinatorial synthesis of N ‐glycosyl conjugates is vital for many fields of modern synthetic organic chemistry. Herein, we report a multicomponent domino process for the regioselective synthesis of a large array N ‐glycosyl‐Asp‐urea conjugates, which could be further functionalized in a chemoselective way, starting from easily accessible reactants such as N ‐glycosylamines, fumaric acid monoesters, azides, and isocyanates. The process occurs under very mild conditions, does not require the use of strong bases/acids or high temperature, and is highly versatile, working efficiently with a range of protecting groups and substituents.