Hydrogen-Bond-Mediated Aglycone Delivery: Synthesis of β-d-Fructofuranosides

Org Lett. 2020 Apr 17;22(8):2967-2971. doi: 10.1021/acs.orglett.0c00702. Epub 2020 Mar 30.

Abstract

The construction of β-d-fructofuranosidic linkages is one of the major challenges in carbohydrate chemistry. In this work, we developed an efficient method for the synthesis of β-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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fructose / analogs & derivatives
  • Fructose / chemical synthesis*
  • Fructose / chemistry
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Hydrogen Bonding
  • Molecular Conformation
  • Thioglycosides / chemistry*

Substances

  • Furans
  • Thioglycosides
  • Fructose