Regioselective synthesis of new sucrose derivatives via 3-ketosucrose

✍ Scribed by Martina Pietsch; Martin Walter; Klaus Buchholz

• Book ID: 102998465
• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 906 KB
• Volume: 254
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(94)84251-5

✦ Synopsis

3-Ketosucrose

(a-D-r&o-hexopyranosyl-3-ulose-~-o-fructofuranoside), obtained from sucrose via microbial oxidation with Agrobactetizun tumefaciens, was shown to be an appropriate and versatile synthon for regioselective syntheses. Condensation with hydroxylamine and its derivatives with ally1 and betray1 groups leads to the oxime and the corresponding substituted products. By reductive amination 3-amino-3-deoxy-&o-allopyranosyl-B-D_6rranoside is obtained which can readily be submitted to further functionalization to methacryloyl and fatty acid derivatives. After silylation of 3-ketosucrose the 3-ally1 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.