Regioselective synthesis of new sucrose derivatives via 3-ketosucrose.
3-Ketosucrose (alpha-D-ribo-hexopyranosyl-3-ulose-beta-D-fructofuranoside), obtained from sucrose via microbial oxidation with Agrobacterium tumefaciens, was shown to be an appropriate and versatile synthon for regioselective syntheses. Condensation with hydroxylamine and its derivatives with allyl and benzyl groups leads to the oxime and the corresponding substituted products. By reductive amination 3-amino-3-deoxy-alpha-D-allopyranosyl-beta-D-fructofuranoside is obtained which can readily be submitted to further functionalization to methacryloyl and fatty acid derivatives. After silylation of 3-ketosucrose the 3-allyl and butylene-substituted as well as decyl- and dodecyl-substituted sucrose can be obtained via Grignard reaction, the side chains being C-C linked to the saccharide.
Pietsch
M
M
Institut für Technologie der Kohlenhydrate an der Technischen Universität Braunschweig-Sugar Institute, Germany.
Walter
M
M
Buchholz
K
K
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D007202:Indicators and Reagents; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009904:Optical Rotation; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; C059956:3-ketosucrose; D013395:Sucrose