An improved synthesis of an umbelliferyl 5-thioxylopyranoside, precursor of the antithrombotic drug Iliparcil
| Autor: | Jean-Pierre Praly, Michel Baudry, Gérard Descotes, Khan Ou, Yolande Collette, Veronique Barberousse, Joaquim Pires |
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| Rok vydání: | 1999 |
| Předmět: |
Drug
Glycosylation Molecular Structure Optical Rotation Chemistry media_common.quotation_subject Organic Chemistry Halide General Medicine Biochemistry Combinatorial chemistry Analytical Chemistry chemistry.chemical_compound Orally active Fibrinolytic Agents Coumarins Bromide Yield (chemistry) Antithrombotic Organic chemistry Benzopyrans Indicators and Reagents Fibrinolytic agent media_common |
| Zdroj: | Carbohydrate Research. 318:162-166 |
| ISSN: | 0008-6215 |
| Popis: | 4-Ethyl-2-oxo-2H-1-benzopyran-7-yl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside, a synthetic intermediate of the orally active antithrombotic compound Iliparcil, has been prepared in 44-47% isolated yield. Different conditions were used for the glycosylation of 4-ethyl-2H-7-hydroxy-1-benzopyran-2-one 6 applying 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide (2), the analogous beta-chloride 3 or the alpha-trichloroacetimidate 5 as donors. With halides 2 and 3, the reaction was carried out in the presence of ZnO-ZnCl2 or ZnO alone. Both promoters are cheap, safe and therefore compatible with large-scale industrial processes. |
| Databáze: | OpenAIRE |
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