title: Synthesis and characterization of the hexenuronic acid model methyl 4-deoxy-beta-L-threo-hex-4-enopyranosiduronic acid.
abstract: A facile synthetic scheme for the preparation of methyl 4-deoxy-beta-L-threo-hex-4-enopyranosiduronic acid utilizing the commercially available methyl alpha-D-galactopyranoside as starting material has been developed. The synthesis sequence comprises six high yielding reaction steps: TEMPO oxidation, acetylation, methanolysis of the lactone, acetylation, beta-elimination, and final removal of the protecting groups. Only one column chromatographic purification is needed throughout the whole sequence. The overall yield is 60%. The final product has been characterized by NMR, Raman, UVRR, FTIR, and HRMS.
authors.affiliation: Helsinki University of Technology, Department of Forest Products Technology, PO Box 6300, FIN-02015 HUT, Finland. iadorjan@cc.hut.fi
authors.forename: Immanuel
authors.initials: I
authors.lastname: Adorjan
authors.forename: Anna-Stiina
authors.initials: AS
authors.lastname: Jääskeläinen
authors.forename: Tapani
authors.initials: T
authors.lastname: Vuorinen
mesh_terms: D002236:Carbohydrate Conformation; D002845:Chromatography; D005690:Galactose / Q000031:analogs & derivatives / Q000737:chemistry; D006603:Hexuronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013059:Spectrum Analysis, Raman; D014574:Uronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D006603:Hexuronic Acids; D014574:Uronic Acids; C095263:hexenuronic acid; C517098:methyl 4-deoxy-beta-L-threo-hex-4-enopyranosiduronic acid; C469243:methyl-galactopyranoside; D005690:Galactose