Gold-catalyzed glycosidation for the synthesis of trisaccharides by applying the armed–disarmed strategy

Abstract

The synthesis of oligosaccharides is still a challenging task as there is no universal glycosyl donor for the synthesis of all oligosaccharides. The gold catalysis for glycosidation reactions, in which alkynylated glycosides are used, has emerged as one of the versatile options in this regard. A cleavage of the interglycosidic bond that was thought to be due to the higher reaction temperature and the acidic medium was observed during the synthesis of trisaccharides. In addition, a very little percentage of deprotection of benzyl protecting groups at the C-6 position was observed and no deprotection of benzyl ethers in aliphatic molecules was noticed. In order to overcome this fact, a collection of leaving groups that contain an alkynyl moiety were screened. It was found that 1-ethynylcyclohexanyl (Ech) glycosides are suitable for carrying out the glycosidation at 25 °C in the presence of 5 mol % each of AuCl3 and AgSbF6. Subsequently, Ech-glycosides were observed to be suitable for the synthesis of trisaccharides under gold catalysis conditions.

Keywords

• alkynes
• armed–disarmed effect
• glycosidation
• gold