Insight into gold-catalyzed glycosylation of glycosyl ynenoates

Abstract

Gold-catalyzed glycosylation using alkyne donors is a versatile approach for the efficient assembly of diverse types of glycosides due to its catalytic and mild glycosylation properties. Minor structural alterations might significantly affect the glycosylation reaction when the alkyne-based leaving groups are simplified. By mapping the glycosylation reactivities of a series of structurally simplified alkyne donors, herein we demonstrate the role of each characteristic functional group of glycosyl ynenoates. Based on the isolation and the X-ray diffraction characterization of the pyran-5-ylgold(I) complex generated from the leaving group, a plausible mechanism of the gold(I)-catalyzed glycosylation with glycosyl ynenoates as donors was proposed.

Graphical abstract

Keywords:

• Alkyne donors
• carbohydrates
• glycosylation
• glycosides
• gold

Disclosure statement

No potential conflict of interest was reported by the author(s).

Supplemental material

Copies of NMR spectra for all pure compounds. This material is available free of charge via the internet at https://www.tandfonline.com/.

Additional information

Funding

Financial support from the National Natural Science Foundation of China (22071054, 21871081), the Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism (Shanghai Municipal Education Commission), the Taishan Industrial Experts Program (tscx202312168), and the Opening Project of Shanghai Key Laboratory of New Drug Design (21DZ2271600) is gratefully acknowledged.