74808-11-0

Upstream product

• 106-44-5 p-cresol 
• 339276-14-1 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 17902-32-8 trimethyl(4-methylphenoxy)silane 
• 89825-08-1 2,3,4,6-tetra-O-benzyl-1-O-trimethylsilyl-α,β-D-glucopyranose 

Relevant academic research and scientific papers

Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O-Glycosylation of 1-O-Acetyl Sugars as Glycosyl Donors

We have developed a new catalyst system comprising AuCl3 and phenylacetylene that promotes the Ferrier rearrangement of glycals and 2-acetoxymethylglycals with different nucleophiles, and also the O-glycosylation of 1-O-acetyl sugars to obtain a variety of useful glycosides at room temperature through relay catalysis. Good anomeric selectivity was observed for the Ferrier rearrangements, whereas the O-glycosylation of 1-O-acetyl sugars gave mixtures of diastereomers with moderate to excellent selectivity.

Aryl C-glycosylation of phenols with glycosyl trifluoroacetimidates

Aryl C-glycosylation of a variety of phenols with glycosyl trifluoroacetimidates in the presence of TMSOTf was examined, leading to the corresponding ortho-hydroxyaryl C-glycosides in variable yields.

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)