TMSCl as a mild and effective source of acidic catalysis in fischer glycosidation and use of propargyl glycoside for anomeric protection

Abstract

Practical Fischer glycosidation was effected at room temperature or 60°C by using 5 to 10 equiv. of TMSCl. The anomeric propargyl group formed by this method was found to be a versatile new protecting group, being stable in neat TFA but readily cleaved by treatment with Co2(CO)8 and TFA in CH2Cl2via the formation of an alkyne–Co complex. © 2002, Taylor & Francis Group, LLC. All rights reserved.