Synthesis of the 3-methyl ether and 4-deoxy derivatives of 4-cyanophenyl 1,5-dithio-β-d-xylopyranoside (Beciparcil)
| Autor: | Soth Samreth, Veronique Barberousse, Francois Bellamy, Yun Li, Derek Horton |
|---|---|
| Rok vydání: | 1999 |
| Předmět: |
chemistry.chemical_classification
Magnetic Resonance Spectroscopy Molecular Structure Stereochemistry Organic Chemistry Iodide Acetal chemistry.chemical_element Ether General Medicine Methylation Borohydride Iodine Biochemistry Mass Spectrometry Analytical Chemistry Structure-Activity Relationship chemistry.chemical_compound Fibrinolytic Agents chemistry Nitriles Epimer Chromatography Thin Layer Glycosides Fibrinolytic agent |
| Zdroj: | Carbohydrate Research. 316:104-111 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/s0008-6215(99)00045-2 |
| Popis: | Treatment of the 2,3-isopropylidene acetal of the title dithioxyloside with 2,4,5-triiodoimidazole-PPh3 caused replacement of the 4-hydroxyl group by iodine to afford 82% of the 4-axial iodide 6, converted by base into 4-cyanophenyl 2,3-O-isopropylidene-1,5-dithio-beta-D-glycero-pent-3-enopyranoside++ + (8). Acid treatment of 8 gave 87% of the deacetonated glycos-3-ulose, borohydride reduction of which afforded 63% of 4-cyanophenyl 4-deoxy-1,5-dithio-alpha-L-threo-pentopyranoside (3), together with 27% of the 3-axial epimer. The 3-methyl ether of the title dithioxyloside was satisfactorily prepared via 2,4-protection as the cyclic phenylboronate, methylation, and deprotection; alternative strategy via the 2,4-bis(triisopropylsilyl) ether was complicated because of silyl-group migration under methylation conditions. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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