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

Article abstract of DOI:10.1016/0008-6215(94)84250-7

Reaction of propargylaldehyde diethyl acetals 1, 2, 3, and 4 and 2,3,4,6-tetra-O-acetyl-1-O-trimethylsilyl-β-D-glucopyranose 5a in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate at -78 deg C gives the acetylated acetal-β-glucosides 6-9 in 60-90percent yield with retention of configuration at C-1.Likewise 2,3,4,6-tetra-O-acetyl-1-O-trimethylsilyl-β-D-glucopyranose 5a afforded, after in situ anomerisation to 5b with 4, the corresponding acetal-α-glucoside 10.Hydrogenation and subsequent deprotection yielded the highly acid-sensitive 2-alkenyl-1-ethoxy glucosides which are of interest as selective anticancer agents.