Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides.
Inexpensive and readily available sulfonic acids, p-toluenesulfonic acid, and sulfuric acid are versatile and efficient catalysts for the peracetylation of a broad spectrum of carbohydrate substrates in good yield and in a practical time frame. Three appealing features in sulfonic acid-catalyzed acetylation of free sugars were explored including (1) suppression of furanosyl acetate formation for D-galactose and L-fucose; (2) high yielding chemoselective acetylation of sialic acid under appropriate conditions; and (3) peracetylation of amino sugars with different amino protecting functions. Simple one-pot two step acetylation-thioglycosidation methods for the expeditious synthesis of p-tolyl per-O-acetyl thioglycosides were also delineated.
Chao
Chin-Sheng
CS
Department of Applied Chemistry, National Chiao Tung University, 1001 Ta-Hsueh Road, Hsinchu 300, Taiwan, ROC.
Chen
Min-Chun
MC
Lin
Shih-Che
SC
Mong
Kwok-Kong T
KK
D000107:Acetylation; D001557:Benzenesulfonates / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D013451:Sulfonic Acids / Q000737:chemistry*; D013464:Sulfuric Acids / Q000737:chemistry; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D014312:Trisaccharides / Q000737:chemistry; D047392:beta-Cyclodextrins / Q000737:chemistry
D001557:Benzenesulfonates; D002241:Carbohydrates; D004187:Disaccharides; D009005:Monosaccharides; D013451:Sulfonic Acids; D013464:Sulfuric Acids; D013865:Thioglycosides; D014312:Trisaccharides; D047392:beta-Cyclodextrins; C031215:betadex; C033158:sulfuric acid; C029501:4-toluenesulfonic acid; C005190:melezitose