title: Simple preparations of alkyl and cycloalkyl alpha-glycosides of maltose, cellobiose, and lactose.
abstract: Alkyl, cycloalkyl, allyl, 4-pentenyl, and benzyl alpha-glycosides of maltose, cellobiose, and lactose were prepared (17-77% yield; alpha/beta=70/30-96/4) via a direct reaction of the free disaccharides with a binary AcBr-AcOH mixture, followed by glycosidation with alcohol using FeCl3 in MeNO2 or CH2Cl2, Zemplén deacetylation, and resolution of the anomeric mixture of glycosides by chromatography. Using MeCN as solvent for the glycosidation step, the corresponding beta-biosides were also prepared (16-61% yield; alpha/beta=25/75-5/95).
authors.affiliation: School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo 108-8641, Japan. kotos@pharm.kitasato-u.ac.jp
authors.forename: Shinkiti
authors.initials: S
authors.lastname: Koto
authors.forename: Motoko
authors.initials: M
authors.lastname: Hirooka
authors.forename: Takako
authors.initials: T
authors.lastname: Tashiro
authors.forename: Motokazu
authors.initials: M
authors.lastname: Sakashita
authors.forename: Masaharu
authors.initials: M
authors.lastname: Hatachi
authors.forename: Takayuki
authors.initials: T
authors.lastname: Kono
authors.forename: Miho
authors.initials: M
authors.lastname: Shimizu
authors.forename: Nahoko
authors.initials: N
authors.lastname: Yoshida
authors.forename: Sayaka
authors.initials: S
authors.lastname: Kurasawa
authors.forename: Natsuko
authors.initials: N
authors.lastname: Sakuma
authors.forename: Sunao
authors.initials: S
authors.lastname: Sawazaki
authors.forename: Akihiro
authors.initials: A
authors.lastname: Takeuchi
authors.forename: Naomi
authors.initials: N
authors.lastname: Shoya
authors.forename: Emi
authors.initials: E
authors.lastname: Nakamura
mesh_terms: D000478:Alkylation; D002475:Cellobiose / Q000737:chemistry*; D003500:Cyclization; D004187:Disaccharides / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D007785:Lactose / Q000737:chemistry*; D008320:Maltose / Q000737:chemistry*
chemical_list: D004187:Disaccharides; D006027:Glycosides; D002475:Cellobiose; D008320:Maltose; D007785:Lactose