Directed SN2 Glycosylation Employing an Amide-Functionalized 1‑Naphthoate Platform Featuring a Selectivity-Safeguarding Mechanism

• Published in: Journal of the American Chemical Society Vol. 145; no. 22; pp. 11921 - 11926
• Main Authors: Ma, Xu, Zhang, Yongliang, Zhu, Xijun, Wei, Yongliang, Zhang, Liming
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 25.05.2023; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; glycosides; glycosylation; hydrogen bonding; oligosaccharides; Physical Sciences; Science & Technology; STEREOSELECTIVE GLYCOSYLATION; BETA-MANNOSYLATION; GLYCOSIDATION REACTIONS

This work implements a catalytic SN2 glycosylation by employing an amide-functionalized 1-naphthoate platform as a latent glycosyl leaving group. Upon gold-catalyzed activation, the amide group enables the SN2 process by directing the attack of the glycosyl acceptor via H-bonding interaction, which...