37812-69-4

Upstream product

• 18081-08-8 2-naphthyl trimethylsilyl ether 
• 89825-07-0 1-O-trimethylsilyl-2,3,4,6-tetra-O-acetyl-D-glucoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 32316-92-0 naphthalene-2-boronic acid 

Downstream Products

• 25320-79-0 [2]naphthyl-α-D-glucopyranoside 
• 6044-30-0 naphthyl-beta-D-glucopyranoside 

Relevant academic research and scientific papers

EINFACHE UND STEREOSELEKTIVE SYNTHESE VON α- UND β-PHENYLGLYKOSIDEN

Reaction of phenyl-trimethylsilylethers (3) with 1-O-trimethylsilyl-2,3,4,6-tetra-O-acetyl-D-glucoside (1) (anomeric mixture) yields almost exclusively the aryl-β-glucosides (4) in the presence of catalytic amounts of TMS-triflate at 20 deg C, whereas (3)

Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature

Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose, and it was demonstrated here how the interaction between carbohydrates and boronic acids can be combined with copper catalysis to achieve selective anomeric O-arylation.