Protecting-group- and microwave-free synthesis of β-glycosyl esters and aryl β-glycosides of N-acetyl-d-glucosamine. (1st August 2022)

• Record Type: Journal Article
• Authors: Hamaya, Yu; Komura, Naoko; Imamura, Akihiro; Ishida, Hideharu; Ando, Hiromune; Tanaka, Hide-Nori
• Is Part Of: Bioorganic & medicinal chemistry. Volume 67(2022)
• Publication Date: 2022-08-01
• Subjects: Protecting-group-free synthesis -- N-acetyl-d-glucosamine oxazoline -- β-glycosyl esters -- Aryl β-glycosides -- Oxazoline ring opening; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2022.116852
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Highlights: Protecting-group-free glycosylation via oxazoline ring opening. Spontaneous reaction of GlcNAc oxazoline with carboxylic acids and phenols. Stereoselective synthesis of β-glycosyl esters and aryl β-glycosides of GlcNAc. Simple, green, and microwave-free glycosylation. Abstract: A protecting-group-free method for synthesis of β-glycosyl esters and aryl β-glycosides was developed by using latent chemical reactivity of N -acetyl-d -glucosamine (GlcNAc) oxazoline. The GlcNAc oxazoline was spontaneously reacted with carboxylic acids and phenol derivatives via the oxazoline ring opening without the use of a catalyst or heating conditions (i.e., microwave irradiation), affording the desired products in moderate to excellent yields with β-selectivity. This simple protecting-group-free method exhibits a wide substrate scope and good functional group tolerance, and it allows the efficient production of a novel class of GlcNAc-conjugated biomaterials and prodrug candidates.