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Conversion of 2,6-anhydro-D-altrose and--mannose derivatives with 4-substituted phenyl thiols to prepare compounds with potential antithrombotic activity.
- Source :
-
Carbohydrate research [Carbohydr Res] 2001 Jun 04; Vol. 332 (3), pp. 325-33. - Publication Year :
- 2001
-
Abstract
- 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.
- Subjects :
- Administration, Oral
Animals
Disease Models, Animal
Fibrinolytic Agents pharmacology
Hexoses chemical synthesis
Magnetic Resonance Spectroscopy
Mannose analogs & derivatives
Mannose chemical synthesis
Mannose pharmacology
Rats
Stereoisomerism
Sulfhydryl Compounds chemical synthesis
Sulfhydryl Compounds pharmacology
Sulfides chemical synthesis
Sulfides pharmacology
Thrombosis drug therapy
Fibrinolytic Agents chemical synthesis
Hexoses pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 0008-6215
- Volume :
- 332
- Issue :
- 3
- Database :
- MEDLINE
- Journal :
- Carbohydrate research
- Publication Type :
- Academic Journal
- Accession number :
- 11376612
- Full Text :
- https://doi.org/10.1016/s0008-6215(01)00102-1