Nucleophilic substitution at the anomeric position of furanose carbohydrates. The case of the C-allylations

Abstract

Taking advantage of the locked conformation of cyclic furanose form, carbohydrate derivatives have been transformed into relevant tetrahydrofuran moieties through a chemical operation commonly known as C-glycosylation reaction. Consequently, a large number of total synthesis of naturally occurring products containing this heterocycle have been accomplished by applying this reaction. In this regard, the C-allylation reaction of furanose carbohydrates provides flexible routes for stereoselective anomeric functionalization by incorporating an allyl group, which is eventually re-functionalized into advanced natural product intermediates. Therefore, this mini review deals with the description of the origin of the stereoselectivity and synthetic applications of this type of glycosylation reaction, which can be also called as: "Nucleophilic Substitution at the Anomeric Position", conducted by various research groups including our own group.

Keywords: Anomeric position; C-allylations; Carbohydrates; Chiron approach; Furanoses.