Stereoselective synthesis of 1,1-dialkyl-1-methoxymethyl glucosides (acetal-glucosides).
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.
Tietze
L F
LF
Institut für Organische Chemie der Georg-August Universität, Göttingen, F.R.G.
Fischer
R
R
Lögers
M
M
Beller
M
M
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
D000080:Acetals; D000970:Antineoplastic Agents; D005960:Glucosides; D006027:Glycosides; D007202:Indicators and Reagents; D011355:Prodrugs