title: New alpha-selective thermal glycosylation of acetyl-protected 2-acetamido-2-deoxy-beta-D-glucopyranosyl diphenylphosphinate.
abstract: This paper describes new alpha-selective thermal glycosylation using acetyl-protected 2-acetamido-2-deoxy-beta-D-glucopyranosyl diphenylphosphinate (4) as a glycosyl donor. When the glycosylation of 4 with 1-hexanol was carried out under various conditions, the conditions using trimethylsilyl trifluoromethanesulfonate as a promoter in nitromethane at reflux temperature were most suitable for the formation of the alpha anomer. The glycosylation of 4 with the other common alcohols gave corresponding alpha-glycosides in relatively high yields under the conditions. When cholesterol, a very steric hindered alcohol, was used as a glycosyl acceptor, alpha-glycoside was also produced predominantly.
authors.affiliation: Department of Materials Science and Engineering, Faculty of Engineering, Yamagata University, Yonezawa, Japan. kadokawa@chem.yz.yamagata-u.ac.jp
authors.forename: J
authors.initials: J
authors.lastname: Kadokawa
authors.forename: T
authors.initials: T
authors.lastname: Nagaoka
authors.forename: J
authors.initials: J
authors.lastname: Ebana
authors.forename: H
authors.initials: H
authors.lastname: Tagaya
authors.forename: K
authors.initials: K
authors.lastname: Chiba
mesh_terms: D000107:Acetylation; D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D002236:Carbohydrate Conformation; D006031:Glycosylation; D006358:Hot Temperature; D007202:Indicators and Reagents; D008958:Models, Molecular; D063065:Organophosphonates / Q000737:chemistry*; D010721:Phosphinic Acids; D013816:Thermodynamics
chemical_list: C416841:2-acetamido-3,4,6-tri-O-acetyl-2-deoxyglucopyranosyl diphenylphosphinate; D007202:Indicators and Reagents; D063065:Organophosphonates; D010721:Phosphinic Acids; D000117:Acetylglucosamine