Our first glycosylation attempts will use the Schmidt glycosyl donor, a trichloroacetimidate. The choice of base strongly influences the configuration of the trichloroacetimidate. One thing that I am not yet sure about is what factors determine the configuration of the final product, the glycoside. I have seen some schemes in which retention occurs and others in which inversion occurs, and my tentative view is that it depends on whether or not there is neighboring group participation, but it might also depend on the acidity of the catalyst. As I learn more, I will post it here.
In the Handbook I mentioned in a previous comment, Schmidt wrote, "The anomeric stereochemistry is derived from the anomeric configuration of glycosyl trichloroacetimidates (inversion or retention), anchimeric assistance, the influence of solvents or thermodynamic or kinetic effects....In addition, the nature of the counteranion in catalysts is very influential in controlling the stereoselectivity of the Schmidt glycosidation, as reflected by comparing entries 1 and 2, or 3 and 4 in Table 3.1 , but how the anions work has not yet been understood." Sounds like I will be burning the midnight oil.