GYKI-39541, RGH-1962
Chemical Name: 1-(4-Nitrophenylsulfanyl)-1,5-dithio-beta-D-arabinopyranoside
CAS No. 218907-16-5
项目整合开发状态: Preclinical
项目研究机构: Gedeon Richter (Originator)
合成路线:The thiobenzoylation of the readily available 2,3-O-isopropylidene-5-O-tosyl-L-arabinose diethyl dithioacetal (I) gives the 5-S-thiobenzoate (II),which is treated with HgO and BF3/Et2O in THF/water gives the corresponding aldehyde (III).The cyclization of (III) with NaOMe in methanol affords the cyclic arabinopyranose (IV),which is deprotected with AcOH giving 5-O-benzoyl-beta-D-arabinopyranose (V).The acetylation of (V) with Ac2O yields the triacetate (VI),which is condensed with 4-nitrothiophenol (VII) by means of K2CO3 in refluxing acetone affording the acylated dithio-beta-D-arabinopyranoside (VIII).Finally,this compound is deacylated with NaOMe in MeOH.
📌 参考资料/链接：
参考文献标题:Novel anticoagulant glycosides and pharmaceutical compsns.thereof
文献作者:Szeker,G.; Boros,S.; Szab? G.; Turuczn?Ferwagner,M.; Orb醤,O.; Feher,B.; Soukupn?Kedves,R.; Kenyeres,L.; Kov醕sn?Boz? E.; Barab醩,?; Moravcsik,I.; Kasz醩,E.; Kuszmann,J.(Gedeon Richter Ltd.)
参考来源:WO 9928312
📄 详细内容
合成路线:The thiobenzoylation of the readily available 2,3-O-isopropylidene-5-O-tosyl-L-arabinose diethyl dithioacetal (I) gives the 5-S-thiobenzoate (II),which is treated with HgO and BF3/Et2O in THF/water gives the corresponding aldehyde (III).The cyclization of (III) with NaOMe in methanol affords the cyclic arabinopyranose (IV),which is deprotected with AcOH giving 5-O-benzoyl-beta-D-arabinopyranose (V).The acetylation of (V) with Ac2O yields the triacetate (VI),which is condensed with 4-nitrothiophenol (VII) by means of K2CO3 in refluxing acetone affording the acylated dithio-beta-D-arabinopyranoside (VIII).Finally,this compound is deacylated with NaOMe in MeOH.
参考文献标题:Synthesis of 4-cyanophenyl and 4-nitrophenyl 1,5-dithio-L- and -D-arabinopyranosides possessing antithrombotic activity
文献作者:Bozo,E.; Boros,S.; Kuszmann,J.
参考来源:Carbohydr Res 1998,311(4),191