Stereoselective synthesis of 2-alkynyl and 2-alkenyl-1-ethoxy glucosides — new types of acetal-glycosides for use in the treatment of cancer

✍ Scribed by Lutz F. Tietze; Anja Fischer-Beller

• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 1012 KB
• Volume: 254
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(94)84250-7

✦ Synopsis

Reaction of propargylaldehyde diethyl acetals

1,2,3,

and

4

and

2,3,4,

6-tetra-O-acetyl-l-O-trimethylsilyl-fi-o-glucopyranose 5a in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate at -78°C gives the acetylated acetal-p-glucosides 6-9 in 60-90% yield with retention of configuration at C-l. Likewise 2,3,4,6-tetra-0-ace~lyl-l-O-trimethylsilyl-~-D-glucopyranose 5a afforded, after in situ anomerisation to Sb with 4, the corresponding acetala-glucoside 10. Hydrogenation and subsequent deprotection yielded the highly acid-sensitive 2-alkenyl-1-ethoxy glucosides which are of interest as selective anticancer agents.