Catalyst-Controlled, Site-Selective Sulfamoylation of Carbohydrate Derivatives
Daniel J. Gorelik, Julia A. Turner, Mark S. Taylor
Abstract
Methods for site-selective sulfamoylation of secondary hydroxyl groups in pyranosides are described. Using a boronic acid catalyst, selective installation of a Boc-protected sulfamoyl group at the equatorial position of cis-diols in manno- and galacto-configured substrates has been achieved. Activation of trans-diol groups in gluco- and galacto-configured substrates is also possible by employing an organotin catalyst.
Topics & Concepts
ChemistryCatalysisDiolBoronic acidCarbohydrateCombinatorial chemistryOrganic chemistryCarbohydrate Chemistry and SynthesisSynthesis and Catalytic ReactionsFluorine in Organic Chemistry