Acid-catalysed rearrangement of glycosyl trichloroacetimidates: a novel route to glycosylamines.
A novel route to glycosylamines has been developed. Treatment of glycosyl trichloroacetimidates with TMSOTf under glycosylation conditions, but in the absence of an acceptor, resulted in complete rearrangement of the trichloroacetimidates into the corresponding N-protected-glycosylamines. Reductive cleavage of the trichloroacetyl groups using sodium borohydride provided the desired glycosylamine products.
Center for Molecular Plant Physiology (PlaCe), Plant Biochemistry Laboratory, Department of Plant Biology, Faculty of Life Sciences, Copenhagen University, 40 Thorvaldsensvej, DK-1871 Frederiksberg C, Copenhagen, Denmark.
Kim
K
Larsen
Carl Erik
CE
Olsen
Mohammed Saddik
MS
Motawia
D000081:Acetamides; D000143:Acids; D000606:Amino Sugars / Q000138:chemical synthesis*; D002384:Catalysis; D062845:Chloroacetates; D006031:Glycosylation; D014238:Trichloroacetic Acid / Q000737:chemistry
D000081:Acetamides; D000143:Acids; D000606:Amino Sugars; D062845:Chloroacetates; D014238:Trichloroacetic Acid; C009528:trichloroacetamide