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Stereoretentive Reactions at the Anomeric Position: Synthesis of Selenoglycosides
Author(s) -
Zhu Feng,
O'Neill Sloane,
Rodriguez Jacob,
Walczak Maciej A.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201802847
Subject(s) - anomer , glycoconjugate , stereospecificity , chemistry , coupling reaction , stereochemistry , glycosyl , substrate (aquarium) , selenium , combinatorial chemistry , organic chemistry , biochemistry , catalysis , oceanography , geology
Abstract Reported is the stereospecific cross‐coupling of anomeric stannanes with symmetrical diselenides, resulting in the synthesis of selenoglycosides with exclusive anomeric control. The reaction proceeds without the need for directing groups and is compatible with free hydroxy groups as demonstrated in the preparation of glycoconjugates derived from mono‐, di‐, and trisaccharides and peptides (35 examples). Given its generality and broad substrate scope, the glycosyl cross‐coupling method presented herein can find use in the synthesis of selenium‐containing glycomimetics and glycoconjugates.