title: Selective synthesis of 1,6-anhydro-β-d-mannopyranose and -mannofuranose using microwave-assisted heating.
abstract: The dehydration of d-mannose and the demethanolization of methyl-α-d-mannopyranoside (MαMP) or methyl-α-d-mannofuranoside (MαMF) were examined using microwave-assisted heating for a 3-min irradiation at temperature from 120 to 280°C in ordinary or dry sulfolane without any catalyst. The microwave-assisted heating of MαMP and MαMF smoothly proceeded to selectively afford the anhydromannoses, 1,6-anhydro-β-d-mannopyranose (AMP) and 1,6-anhydro-β-d-mannofuranose (AMF), respectively, in high yields. For MαMP in ordinary sulfolane at 240°C, AMP was selectively obtained in the AMF:AMP ratio of 4:96, whereas AMF was the major product at the AMF:AMP ratio of 97:3 from MαMF in dry sulfolane at 220°C.
authors.affiliation: Graduate School of Engineering, Hokkaido University, Sapporo, Japan.
authors.forename: Nguyen To
authors.initials: NT
authors.lastname: Hoai
authors.forename: Akiyoshi
authors.initials: A
authors.lastname: Sasaki
authors.forename: Masahide
authors.initials: M
authors.lastname: Sasaki
authors.forename: Harumi
authors.initials: H
authors.lastname: Kaga
authors.forename: Toyoji
authors.initials: T
authors.lastname: Kakuchi
authors.forename: Toshifumi
authors.initials: T
authors.lastname: Satoh
mesh_terms: D002849:Chromatography, Gas; D006361:Heating; D008358:Mannose / Q000138:chemical synthesis* / Q000737:chemistry*; D008766:Methylmannosides / Q000737:chemistry; D008872:Microwaves
chemical_list: D008766:Methylmannosides; D008358:Mannose