Our initial hypothesis was that the 3D structure of the glycosyl donor was important for the degree of inversion in the glycosylations. We, therefore, designed two chiral acceptors (scheme 2) to investigate if a match or mismatch was observed upon reaction with the two anomeric donors (1-α and 1-β in Scheme 1). Due to the many chiral centers in carbohydrates, matches and mismatches with other chiral substrates are commonly encountered and exploited within carbohydrate chemistry. Scheme 2: Synthetic route for the chiral acceptors used for the match/mismatch study.