Abstract
The synthesis is described of highly acid-sensitive 1,1-dialkyl-1-methoxymethyl glucosides (acetal-glucosides) as potential anti-cancer prodrugs. Reaction of 2,3,4,6-tetra- O-acetyl-1- O-trimethylsilyl-β- d-glucopyranose ( 4) severally with various aliphatic and alicyclic ketones and methyl trimethylsilyl ether, in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate, afforded the corresponding acetylated acetal-β-glucosides, e.g., acetone gave 1-methoxy-1-methylethyl 2,3,4,6-tetra- O-acetyl-β- d-glucopyranoside ( 7a). Likewise the α-anomer ( 8a) of 7a was obtained from the α-anomer of 4. Deacetylation of the tetra-acetates then gave the acetal-α- and -β-glucosides.
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