Facile synthesis of N-glycosyl amides using a N-glycosyl-2,4-dinitrobenzenesulfonamide and thioacids.
N-Glucosyl-2,4-dinitrobenzenesulfonamide was prepared from N-acetyl-d-glucosamine and 2,4-dinitrobenzenesulfonyl chloride. Amidation of several thioacids using the N-glucosylsulfonamide donor proceeded smoothly to give the desired N-glucosylamides in good to high yields. The amidation reactions were carried out at room temperature, under mild conditions, and were completed in a very short time.
Talan
Rommel S
RS
Department of Chemistry, The University of Toledo, OH 43606, United States.
Sanki
Aditya K
AK
Sucheck
Steven J
SJ
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000577:Amides; D006027:Glycosides; D013438:Sulfhydryl Compounds