title: An update of the rules for pyranoside sulfonate displacement.
abstract: The original 1967 Richardson-Hough rules for predicting SN2 displacement viability in carbohydrate sulfonate derivatives with external nucleophiles have now been updated. Not only do the original rules still hold, but the newly updated rules rationalize why O-triflates (trifluoromethanesulfonate esters) frequently allow many seemingly "disallowed" pyranosidic nucleophilic substitutions to proceed. The new guidelines, which are based on three decades of experimental evidence, allow the feasibility of many pyranosidic O-triflate SN2 displacements to be gauged beforehand.
authors.affiliation: The School of Chemistry & Chemical Engineering and the Centre for Cancer Research and Cell Biology (CCRCB), the Queen's University Belfast , Stranmillis Road, Belfast BT9 5AG, Northern Ireland, United Kingdom.
authors.forename: Karl J
authors.initials: KJ
authors.lastname: Hale
authors.forename: Leslie
authors.initials: L
authors.lastname: Hough
authors.forename: Soraya
authors.initials: S
authors.lastname: Manaviazar
authors.forename: Andrew
authors.initials: A
authors.lastname: Calabrese
mesh_terms: D000476:Alkanesulfonates / Q000737:chemistry; D004952:Esters; D006027:Glycosides / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000476:Alkanesulfonates; D004952:Esters; D006027:Glycosides; D008698:Mesylates; C012077:trifluoromethanesulfonic acid