Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides

• Published in: Carbohydrate research Vol. 343; no. 5; pp. 957 - 964
• Main Authors: Chao, Chin-Sheng, Chen, Min-Chun, Lin, Shih-Che, Mong, Kwok-Kong T.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 07.04.2008; Elsevier
• Subjects: Acetylation; Acid-catalyzed acetylation; Amino sugars; Benzenesulfonates - chemistry; beta-Cyclodextrins - chemistry; Biochemistry & Molecular Biology; Carbohydrates - chemical synthesis; Carbohydrates - chemistry; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; Disaccharides - chemical synthesis; Disaccharides - chemistry; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Molecular Structure; Monosaccharides - chemical synthesis; Monosaccharides - chemistry; One-pot protecting group manipulation; p-Toluenesulfonic acid; Physical Sciences; Science & Technology; Sulfonic Acids - chemistry; Sulfuric Acids - chemistry; Thioglycosides - chemical synthesis; Thioglycosides - chemistry; Trisaccharides - chemistry; One-pot protecting group manipulation; p-Toluenesulfonic acid; Acid-catalyzed acetylation; Amino sugars; amino sugars; ACETOLYSIS; AZIDES; ACYLATION; DONORS; PER-O-ACETYLATION; one-pot protecting group manipulation; p-toluenesulfonic acid; CHEMICAL SYNTHESIS; ALCOHOLS; UNPROTECTED REDUCING SUGARS; acid-catalyzed acetylation; EFFICIENT CATALYST; OLIGOSACCHARIDE SYNTHESIS
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2008.01.014

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.