title: Stereoselective synthesis of 1,1-dialkyl-1-methoxymethyl glucosides (acetal-glucosides).
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-beta-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-beta-glucosides, e.g., acetone gave 1-methoxy-1-methylethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (7a). Likewise the alpha-anomer (8a) of 7a was obtained from the alpha-anomer of 4. Deacetylation of the tetra-acetates then gave the acetal-alpha- and -beta-glucosides.
authors.affiliation: Institut für Organische Chemie der Georg-August Universität, Göttingen, F.R.G.
authors.forename: L F
authors.initials: LF
authors.lastname: Tietze
authors.forename: R
authors.initials: R
authors.lastname: Fischer
authors.forename: M
authors.initials: M
authors.lastname: Lögers
authors.forename: M
authors.initials: M
authors.lastname: Beller
mesh_terms: D000080:Acetals / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D002236:Carbohydrate Conformation; D015195:Drug Design; D005960:Glucosides / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009904:Optical Rotation; D011355:Prodrugs / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000970:Antineoplastic Agents; D005960:Glucosides; D006027:Glycosides; D007202:Indicators and Reagents; D011355:Prodrugs