Aryl Sulfonates in Inversions at Secondary Carbohydrate Hydroxyl Groups: A New and Improved Route Toward 3-Azido-3-deoxy-β-d-galactopyranosides

GRAPHICAL ABSTRACTAryl Sulfonates in Inversions at Secondary Carbohydrate Hydroxyl Groups: A New and Improved Route Toward 3-Azido-3-deoxy-β-d-galactopyranosidesAll authorsKristoffer Peterson, Alex Weymouth-Wilson & Ulf J. Nilssonhttps://doi.org/10.1080/07328303.2015.1105248Published online:30 November 2015A method of using benzenesulfonates and imidazylates as leaving groups at the secondary C3 galactopyranose carbon, instead of the commonly used less stable triflate leaving group, to facilitate scale-up and improve reproducibility is disclosed. The benzenesulfonates and imidazylates were proven to be significantly more stable than the corresponding triflates and the method was used to devise an improved route toward 3-azido-3-deoxy-β-d-galactopyranosides.