Synthesis of deoxy sugar esters: a chemoenzymatic stereoselective approach affording deoxy sugar derivatives also in the form of aldehyde.
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.
Villo
Ly
L
Department of Chemistry, Tallinn University of Technology, Ehitajate tee 5, 19086 Tallinn, Estonia. lee@chemnet.ee
Danilas
Kady
K
Metsala
Andrus
A
Kreen
Malle
M
Vallikivi
Imre
I
Vija
Sirje
S
Pehk
Tõnis
T
Saso
Luciano
L
Parve
Omar
O
D000447:Aldehydes / Q000737:chemistry*; D003837:Deoxy Sugars / Q000138:chemical synthesis*; D004952:Esters; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
D000447:Aldehydes; D003837:Deoxy Sugars; D004952:Esters