Stereoselective synthesis of (1-alkoxyalkyl) α- and β-d-glucopyranosiduronates (acetal-glucopyranosiduronates): A new approach to specific cytostatics for the treatment of cancer

✍ Scribed by Lutz F. Tietze; Rainer Seele; Barbara Leiting; Thomas Krach

• Publisher: Elsevier Science
• Year: 1988
• Tongue: English
• Weight: 685 KB
• Volume: 180
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(88)80082-x

✦ Synopsis

The reaction of methyl 2,3,4,6-tetra-O-acetyl-l-O-trimethylsilyl-~-(5) andcr-D-glucopyranuronate (6) severally with the dimethyl or diethyl acetals of formaldehyde, bromoacetaldehyde, propionaldehyde, 3-benzyloxypropionaldehyde, 5carboxypentanal, and 2-bromohexanal in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate at -78" gave the corresponding (lalkoxyalkyl) (Y-and @glycosides (acetal-glucopyranosiduronates) with retention of configuration at C-l in yields of 41-91%. Instead of the dialkyl acetals, the corresponding aldehydes and alkyl trimethylsilyl ether can be used. Deacetylation gave the corresponding methyl (acetal-p-and -a-D-glucopyranosid)uronates in good yield. De-esterification of methyl [(lR)-1-methoxybutyl P-o-glucopyranosid]uronate with esterase gave the acetal-P-D-glucopyranosiduronic acid which was an excellent substrate for P-D-glucuronidase. *Glycosidation, Part 8. For Part 7, see ref. 1.