Fe(III)-catalyzed stereoselective synthesis of deoxyglycosides using stable bifunctional deoxy-phenylpropiolate glycoside donors

Carbohydr Res. 2024 Feb 2;536:109051. doi: 10.1016/j.carres.2024.109051. Online ahead of print.ABSTRACTHerein, we report a mild and economical route for the stereoselective synthesis of 2-deoxy and 2,6-dideoxyglycosides via FeCl3-catalyzed activation of bench stable deoxy-phenylpropiolate glycosyl donors (D-PPGs). Optimized reaction conditions work well under additive-free conditions to afford the corresponding 2-deoxy and 2,6-dideoxyglycosides in good yields with high α-anomeric selectivity by reacting with sugar and non-sugar-based acceptors. The optimized conditions were also extended for disarmed D-PPG donors. In addition, the developed strategy is amenable to high-scale-up synthesis.PMID:38325069 | DOI:10.1016/j.carres.2024.109051
Source: Carbohydrate Research - Category: Genetics & Stem Cells Authors: Source Type: research