High-pressure glycosylations of unreactive alcohols and the formation of N-glycosyl collidinium salts.
The yields of disaccharide glycosylation products in tetramethylammonium bromide or silver triflate-collidine activated reactions between hindered alcohols and glycosyl halides were not greatly ++affected when a pressure of 15 kbar was applied. The formation of orthoester products was greatly increased under pressure. When orthoester formation was not possible both disaccharides and the related N-glycosyl collidinium salts were found.
Dauben
W G
WG
Department of Chemistry, University of California, Berkeley 94720.
Köhler
P
P
D000438:Alcohols / Q000737:chemistry*; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis; D006031:Glycosylation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D012492:Salts / Q000138:chemical synthesis
D000438:Alcohols; D004187:Disaccharides; D011725:Pyridines; D012492:Salts; C007106:gamma-collidine