Reaction of Peracylated Sugars with Nitriles Catalyzed by Lewis Acids
- 1 November 1995
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 14 (8) , 1209-1216
- https://doi.org/10.1080/07328309508005405
Abstract
The reaction of acetylaminoacetonitrile with penta-O-benzoyl-α-D-glucopyranose in dichloromethane-nitromethane, in a 1:1 stoichiometric proportion, catalysed by stannic chloride, gave a nitrilium salt that, after hydrolysis, afforded the corresponding N-acyl glycosylamine and a mixture of several compounds originating from different competitive reactions. Among these compounds, N-benzoyl-3,5,6-tri-O-benzoyl-β-D-glucofuranosyl amine, tetra-O-benzoyl-D-glucopyranose, and octa-O-benzoyl-β-D-glucopyranosyl-(1→1)-α-D-glucopyranoside (octa-O-benzoyl-α,β-trehalose) were identified.Keywords
This publication has 12 references indexed in Scilit:
- Ritter-like reactions of 1,2-anhydropyranose derivativesThe Journal of Organic Chemistry, 1991
- Generation of α-D-glucopyranosylacetonitrilium ions. Concerning the reverse anomeric effectJournal of the Chemical Society, Perkin Transactions 1, 1990
- O-(α-D-Glucopyranosyl)trichloroacetimidate as a Glucosyl DonorJournal of Carbohydrate Chemistry, 1985
- Synthesis of N-glycosides. Formation of glucosylamine by reaction of 2,3,4,6-tetra-O-benzyl-D-glucopyranose with acetonitrile in the presence of trifluoromethanesulfonic anhydrideThe Journal of Organic Chemistry, 1981
- Stereoselective glycosidations of uronic acidsTetrahedron Letters, 1980
- The azidonitration of tri-O-acetyl-D-galactalCanadian Journal of Chemistry, 1979
- Conversion of alcohols into amides using chlorodiphenylmethylium hexachloroantimonate in nitrile solventsJournal of the Chemical Society, Chemical Communications, 1973
- Nitrilium salts. New method for the synthesis of secondary aminesThe Journal of Organic Chemistry, 1969
- Electrophilic Catalysis in Nucleophilic Substitution and Elimination. IV. Kinetics of Reaction of 2-Octyl Bromide with Tetraethylammonium and Silver Perchlorates and Nitrites in Acetonitrile1,2Journal of the American Chemical Society, 1965
- A New Reaction of Nitriles. I. Amides from Alkenes and Mononitriles1Journal of the American Chemical Society, 1948