Synthesis and characterization of the hexenuronic acid model methyl 4-deoxy-beta-L-threo-hex-4-enopyranosiduronic acid.
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.
Adorjan
Immanuel
I
Helsinki University of Technology, Department of Forest Products Technology, PO Box 6300, FIN-02015 HUT, Finland. iadorjan@cc.hut.fi
Jääskeläinen
Anna-Stiina
AS
Vuorinen
Tapani
T
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*
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