title: Synthesis of deoxy sugar esters: a chemoenzymatic stereoselective approach affording deoxy sugar derivatives also in the form of aldehyde.
abstract: A chemoenzymatic synthesis of deoxy sugar esters is described. The synthesis is based on the O-alkylation of carboxylic acid with 2-bromo-5-acetoxypentanal. The method allows treatment of hydroxy carboxylic acids without protection of alcoholic hydroxyl groups. Several stereoisomeric deoxy sugar esters were resolved (up to ee or de > 98%) using a lipase-catalyzed acetylation of hemiacetals that in certain cases afforded deoxy sugar derivatives in the form of aldehydes. The stereochemistry of the reactions was determined by the NMR spectra of mandelic acid derivatives.
authors.affiliation: Department of Chemistry, Tallinn University of Technology, Ehitajate tee 5, 19086 Tallinn, Estonia. lee@chemnet.ee
authors.forename: Ly
authors.initials: L
authors.lastname: Villo
authors.forename: Kady
authors.initials: K
authors.lastname: Danilas
authors.forename: Andrus
authors.initials: A
authors.lastname: Metsala
authors.forename: Malle
authors.initials: M
authors.lastname: Kreen
authors.forename: Imre
authors.initials: I
authors.lastname: Vallikivi
authors.forename: Sirje
authors.initials: S
authors.lastname: Vija
authors.forename: Tõnis
authors.initials: T
authors.lastname: Pehk
authors.forename: Luciano
authors.initials: L
authors.lastname: Saso
authors.forename: Omar
authors.initials: O
authors.lastname: Parve
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D003837:Deoxy Sugars / Q000138:chemical synthesis*; D004952:Esters; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
chemical_list: D000447:Aldehydes; D003837:Deoxy Sugars; D004952:Esters