A Metal-free and β-Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides: Synthesis of 5-aza analogues of Aquayamycin

A convenient protocol for β-stereoselective synthesis of 2-deoxy-C-aryl glycosides has been developed. This reaction takes place in one step by using I2/Et3SiH to activate glycosyl acetate to generate glycosyl iodide intermediate in situ, which was captured by naphthol followed by Fries-like O- → C-glycoside rearrangement to selectively afford β-C-aryl glycoside. The approach is applicable to a wide range of naphthol modules, and its utility was demonstrated in the synthesis of 5-aza analogues of Aquayamycin.

Comprehensive structure-activity relationship (SAR) investigation of C-aryl glycoside derivatives for the development of SGLT1/SGLT2 dual inhibitors

Human sodium dependent glucose co-transporters (SGLTs) are the attractive targets for diabetes, and the development of SGLT1/SGLT2 dual inhibitors has received substantial attention in recent years due to their better...

DNA-catalyzed glycosylation using aryl glycoside donors

Using both β and α anomers of aryl glycosides as the glycosyl donors, we used in vitro selection to identify deoxyribozymes that glycosylate 3′-OH of a DNA oligonucleotide.

Correction: DNA-catalyzed glycosylation using aryl glycoside donors

Correction for ‘DNA-catalyzed glycosylation using aryl glycoside donors’ by Anthony R. Hesser et al., Chem. Commun., 2016, 52, 9259–9262.