title: Synthesis of a novel D-glucose-conjugated 15-crown-5 ether with a spiro ketal structure.
abstract: This paper describes a synthetic approach to a novel D-glucose-conjugated 15-crown-5 ether having a spiroketal structure starting from a 1-C-vinylated glucose derivative. The approach consists of the glycosylation of the vinylated glucose derivative to give an ethyleneoxy spacer derivative using bismuth(III) triflate, the conversion of the 1-C-vinyl group of the glucoside produced into a carboxylic acid group, and the intramolecular condensation between the carboxyl group and the terminal hydroxyl group in the ethyleneoxy spacer. A D-glucose-conjugated 15-crown-5 ether having a unique spiroketal structure was thus successfully synthesized.
authors.affiliation: The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo 173-0003, Japan. tyama@noguchi.or.jp
authors.forename: Takashi
authors.initials: T
authors.lastname: Yamanoi
authors.forename: Yoshiki
authors.initials: Y
authors.lastname: Oda
authors.forename: Hitomi
authors.initials: H
authors.lastname: Muraishi
authors.forename: Sho
authors.initials: S
authors.lastname: Matsuda
mesh_terms: D043844:Crown Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans; D005947:Glucose / Q000737:chemistry*; D005960:Glucosides; D006031:Glycosylation; D013141:Spiro Compounds
chemical_list: D043844:Crown Ethers; D005663:Furans; D005960:Glucosides; D013141:Spiro Compounds; C520774:spiroketal; C027792:vinyl glucopyranoside; C042148:15-crown-5; D005947:Glucose
references.citation: Org Biomol Chem. 2004 May 7;2(9):1395-403
references.pmid: 15105932