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.

Highly regioselective and stereoselective synthesis of C-Aryl glycosides via Nickel-catalyzed ortho-C-H glycosylation of 8-aminoquinoline benzamides

C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzed ortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows...

Selective demethylation of O-aryl glycosides by iridium-catalyzed hydrosilylation

The cleavage of alkyl ethers by hydrosilylation is a powerful synthetic tool for the generation of silyl ethers. Previous attempts to apply this transformation to carbohydrate derivatives have been constrained...

Recent advances in the direct O-arylation of carbohydrates

An emerging approach for the synthesis of O-aryl glycosides and carbohydrate-derived aryl ethers via C(sp2)–O bond formation is reviewed.

Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts

An effective Pd(ii)-catalyzed stereoselective C-glycosylation method has been successfully manifested for the synthesis of diversely functionalized 2,3-dideoxy C-aryl glycosides starting from glycals with a wide range of diaryliodonium salts.

Regio- and diastereoselective Pd-catalyzed synthesis of C2-aryl glycosides

A highly regio- and diastereoselective Pd-catalyzed direct arylation reaction of 2,3-glycals is reported.