Having successfully applied our training strategy to R1 and R2, we extended this approach to model the acid-catalysed glycoside bond formation between glucosyl α-trichloroacetate and i -PrOH in explicit DCM, R3 (Fig. ). Controlling the stereoselectivity of glycosylation, a key step in carbohydrate synthesis, remains a significant synthetic challenge (Fig. ). This arises from the range of mechanistic pathways available, ranging from concerted S N 2 to stepwise S N 1-type, the latter involving a transient oxocarbenium intermediate, or an S N i pathway, characterised by a contact ion pair (Fig. ). Both experimental and computational studies 14,66 have shown that stereoselectivity is influenced by multiple factors, including the nature of the leaving group, substituents, temperature, and solvent choice.