Conversion of 2,6-anhydro-D-altrose and--mannose derivatives with 4-substituted phenyl thiols to prepare compounds with potential antithrombotic activity.
Acetolysis of methyl 3,4-di-O-acetyl-2,6-anhydro-D-altropyranoside afforded a mixture containing, besides 1,3,4-tri-O-acetyl-2,6-anhydro-D-altropyranose, the (1R) and (1S) diastereomers of methyl 2,6-anhydro-D-altrose-tetraacetate. Treatment of this mixture with 4-cyanobenzenethiol in the presence of trimethylsilyl triflate resulted in a mixture containing the 3,4,5-tri-O-acetyl-2,6-anhydro-D-altrose bis(4-cyanophenyl) dithioacetal, the corresponding O-methyl S-aryl monothiohemiacetal diastereomers and the beta-thiopyranoside, respectively. Acetolysis of methyl 3,4-di-O-acetyl-2,6-anhydro-D-mannopyranoside led to a mixture of the (1R) and (1S) diastereomers of methyl 2,6-anhydro-D-mannosetetraacetate, which was converted into the corresponding O-methyl S-aryl monothiohemiacetals. Treatment of 1,1,3,4,5-penta-O-acetyl-2,6-anhydro-aldehydo-D-altrose and -D-mannose with 4-cyano- and 4-nitrobenzenethiol, respectively, in the presence of trimethylsilyl triflate afforded the corresponding dithioacetal derivatives. All arylthio derivatives obtained after deacetylation were tested for their oral antithrombotic activity.
Bozó
E
E
Gedeon Richter Chemical Works Ltd., PO Box 17, H-1475, Budapest, Hungary.
Boros
S
S
Kuszmann
J
J
D000284:Administration, Oral; D000818:Animals; D004195:Disease Models, Animal; D005343:Fibrinolytic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006601:Hexoses / Q000138:chemical synthesis / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D051381:Rats; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D013440:Sulfides / Q000138:chemical synthesis / Q000494:pharmacology; D013927:Thrombosis / Q000188:drug therapy
D005343:Fibrinolytic Agents; D006601:Hexoses; D013438:Sulfhydryl Compounds; D013440:Sulfides; D008358:Mannose