Stereoretentive Manipulations of Anomeric Nucleophiles: Applications in the Synthesis of Selenoglycosides.

We report a stereospecific cross-coupling of anomeric stannanes with symmetrical diselenides resulting in the synthesis of selenoglycosides with exclusive anomeric control without directing groups. This reaction is compatible with free hydroxyl groups and was demonstrated in the preparation of glycoconjugates derived from mono-, di- and trisaccharides and peptides (35 examples). Given the generality and a broad substrate scope, the glycosyl cross-coupling method can find use in the synthesis of glycomimetics and glycoconjugates.
PMID: 29671931 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - April 19, 2018 Category: Chemistry Authors: Zhu F, O'Neill S, Rodriguez J, Walczak MA Tags: Angew Chem Int Ed Engl Source Type: research