ChemInform Abstract: An Improved Synthesis of an Umbelliferyl 5-Thioxylopyranoside, Precursor of the Antithrombotic Drug Iliparcil

Autor:	Gérard Descotes, Michel Baudry, Khan Ou, Joaquim Pires, Yolande Collette, Jean-Pierre Praly, Veronique Barberousse
Rok vydání:	2010
Předmět:	Drug chemistry.chemical_compound Glycosylation Orally active chemistry Bromide media_common.quotation_subject Yield (chemistry) Antithrombotic Halide General Medicine Combinatorial chemistry media_common
Zdroj:	ChemInform. 30
ISSN:	1522-2667 0931-7597
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
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9ec0e017dd8e37732446c424d5d4caa2 https://doi.org/10.1002/chin.199952205 Zobrazit plný text záznamu Plný text