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Phosphate esters in polyhydroxylated systems are normally blighted by uncontrolled migration under a variety of reaction conditions. Cesium fluoride is demonstrated as a reagent to control migration of primary phosphates during transesterifications. This allows easy exchange of phosphoryl protecting groups enabling enhanced synthetic strategic flexibility and regioselective phosphate installation. Mechanistic analysis suggests that a fluoride-induced extended solvent sphere modulates steric bulk at phosphorus to favor the primary position.

Original publication

DOI

10.1021/ol303271z

Type

Journal article

Journal

Org Lett

Publication Date

18/01/2013

Volume

15

Pages

346 - 349

Keywords

Cesium, Esterification, Fluorides, Molecular Structure, Stereoisomerism, Sugar Phosphates