Synthesis of Biologically Relevant β‐ N ‐Glycosides by Biphasic Epoxidation‐Aminolysis of D‐Glycals
Year: 2020
Type: article
Abstract: Several β‐ N ‐glycosides were obtained upon a simple and efficient two‐step methodology. First, α‐1,2‐anhydrosugars were prepared diastereoselectively by the oxidation of 3,4,6‐tri‐O‐benzyl‐D‐glucal under biphasic conditions (CH 2 Cl 2 /water) using dimetyldioxirane (DMDO) generated in situ from oxone/acetone mixture and amphiphilic imidazolium ionic liquid (DodMImBF 4 ) as phase transfer catalyst. Immediately, β‐ N ‐glycosides were synthesized in good yields by aminolysis of these α‐1,2‐anhydrosugars using CH 3 CN as solvent. The overall process allows stereoselective generation of biologically relevant carbohydrate derivatives.
Source: ChemistrySelect
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W3021817591