Hydrogen-Bond-Mediated Aglycone Delivery: Synthesis of ß-d-Fructofuranosides.

The construction of ß-d-fructofuranosidic linkages is one of the major challenges in carbohydrate chemistry. In this work, we developed an efficient method for the synthesis of ß-d-fructofuranosides by using a 6-picoloyl-protected fructofuranosyl thioglycoside as the glycosyl donor. Subsequently, we applied the approach to a wide variety of donors and acceptors. Furthermore, the successful synthesis of levantetrose confirmed its applicability in the multistep synthesis of oligosaccharides.