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项目整合精选>>>Brovavir, Sorivudine, BV-araU, SQ-32756, YN-72, BVAU, Bravavir, Usevir
Brovavir, Sorivudine, BV-araU, SQ-32756, YN-72, BVAU, Bravavir, Usevir
索立夫定Chemical Name: (+)-1-beta-D-Arabinofuranosyl-5-[(E)-2-bromovinyl]uracil; (+)-(E)-1-beta-D-Arabinofuranosyl-5-(2-bromoethenyl)-2,4(1H,3H)-pyrimidinedione
CAS No. 77181-69-2
项目整合开发状态: Withdrawn-1995
项目研究机构: Yamasa Shoyu (Originator), Azwell (Licensee), Bristol-Myers Squibb (Licensee), Eisai (Licensee)
合成路线:Treatment of 5-hydroxymethyl-1-beta-D-arabinofuranosyluracil (I) with hydrogen chloride in dioxane affords the 5-chloromethyl derivative (II),which is converted to the triphenylphosphonium salt (III).The Wittig reaction of (III) by means of paraformaldehyde and n-butyllithium in DMF yields the 5-vinyl derivative (IV),and bromination of (IV) with bromine in DMF under a heated condition affords BVAU.
📌 参考资料/链接：
参考文献标题:BVAU
文献作者:Sakata,S.; Machida,H.
参考来源:Drugs Fut 1982,7(7),458
📄 详细内容
合成路线:A new synthesis of BVAU has been described:The condensation of 1-(beta-D-arabinofuranosyl)-5-formyluracil (I) with malonic acid (II) by means of piperidine in hot anhydrous pyridine gives the carboxyvinyl derivative (III),which is then treated with N-bromosuccinimide in basic medium.
参考文献标题:Synthesis of 14C-labelled 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl) uracil (BV-araU)
文献作者:Sakata,S.; Machida,H.; Kumagai,M.; Yamaguchi,T.; Ikeda,K.
参考来源:J Label Compd Radiopharm 1989,27(5),503
合成路线:Treatment of 5-hydroxymethyl-1-beta-D-arabinofuranosyluracil (I) with hydrogen chloride in dioxane affords the 5-chloromethyl derivative (II),which is converted to the triphenylphosphonium salt (III).The Wittig reaction of (III) by means of paraformaldehyde and n-butyllithium in DMF yields the 5-vinyl derivative (IV),and bromination of (IV) with bromine in DMF under a heated condition affords BVAU.
参考文献标题:Synthesis and antiherpes-viral activity of 5-C-substituted uracil nucleosides
文献作者:Senda,S.; Mizuno,Y.; Shibuya,S.; Ikeda,K.; Sakata,S.; Machida,H.; Hirota,K.; Yoshino,H.
参考来源:Nucleic Acids Res Symp Ser 1980,8(8),S39-S42
产品链接: CAS No. 77181-69-2››