1093661-07-4Relevant academic research and scientific papers
Addition reactions of benzenesulfinic acid with glycals and 1,2-dibromosugars
Basava, Vikram,Flores, Broc,Giovine, Matthew,Licisyn, Thomas,Walck, Katelyn,Boyko, Walter,Giuliano, Robert
experimental part, p. 389 - 400 (2009/04/11)
The addition of benzenesulfinic acid to glycals was investigated under various conditions, and optimized yields of the glycosyl phenylsulfone products were obtained in the presence of tin tetrachloride as a catalyst. Double bond shift (Ferrier rearrangement) occurred in all cases except amicetal, which lacks a substituent at the allylic carbon. Glycosylation of benzenesulfinic acid with 1,2-dibromides was carried out using silver triflate as the promoter, and gave sulfinate esters as products by reaction at oxygen rather than at sulfur. The sulfinate esters were obtained as mixtures of stereoisomers at the stereogenic sulfur atom. Trapping of the sulfinates with carboxylate nucleophiles was observed during attempted oxidation with MCPBA. Copyright Taylor & Francis Group, LLC.
