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Practical Fischer glycosidation was effected at room temperature or 60 degrees 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 CH2Cl2 via the formation of an alkyne-Co complex.

TMSCl as a Mild and Effective Source of Acidic Catalysis in Fischer Glycosidation and Use of Propargyl Glycoside for Anomeric Protection