Stereoselective AromaticO-Glycosylation of Glycosyl Chloride with Arylboronic Acid under an Air Atmosphere

Abstract

A novel exclusive β-selective O-aryl glycosylation was developed using glycosyl chloride and arylboronic acid with a palladium catalyst under an air atmosphere. The reaction was insensitive to moisture and characterized using readily available and bench-stable glycosyl chloride and arylboronic acid as substrates. A diverse range of substrate scopes, including various arylboronic acids and glycosyl chloride donors, was well-tolerated in this method. Arylboronic acid was oxidized by O2 in air to produce phenol as the aromatic source. This new strategy provides an alternative route and may find broad applications in efficient synthesis of bioactive O-aryl glycosides in the future.

Expeditious Synthesis of Gwanakoside A and the Chloronaphthol Glycoside Congeners

“…Aromatic O -glycosides are ubiquitous in natural environments, exhibiting a diverse range of biological effects, including antioxidant, anti-inflammatory, antimicrobial, and anticancer properties. The synthesis of phenyl glycosides has attracted significant attention, owing to their potential therapeutic applications and the intricate synthetic challenges associated with these molecules. − The structural variability of phenyl glycosides, influenced by both the phenyl aglycone and the sugar moiety, underscores the importance of adaptable and efficient synthetic methodologies. Such methodologies are essential for realizing the pharmacological potential of these compounds and expanding the repertoire of bioactive substances available for medical applications.…”