Published in

Thieme Gruppe, Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 2023

DOI: 10.1055/a-2186-1485

Links

Tools

Export citation

Search in Google Scholar

Practical Site-selective Oxidation of Glycosides with Pd(OAc)2/Neocuproine

Distributing this paper is prohibited by the publisher
Distributing this paper is prohibited by the publisher

Full text: Unavailable

Red circle
Preprint: archiving forbidden
Orange circle
Postprint: archiving restricted
Red circle
Published version: archiving forbidden
Data provided by SHERPA/RoMEO

Abstract

Palladium-catalyzed oxidation of the secondary C3 hydroxy group in glycopyranosides has set its mark in the selective modification of unprotected carbohydrates. The pre-formed catalyst [(neocuproine)PdOAc]2(OTf)2 oxidizes besides monosaccharides also di-, and oligosaccharides. Here, we provide a more convenient protocol for this reaction in which the Pd-catalyst is formed in situ from Pd(OAc)2 and neocuproine in methanol at 50 °C. Together with a simplified product isolation, this protocol is applied to a series of mono- and disaccharides and has been applied on 10-gram scale. The protocol is also valuable as a screening method to determine whether more extensive studies using the pre-formed catalyst are worthwhile.