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项目整合精选>>>Ladakamycin(formerly), Azacitidine, U-18496, NSC-102816, Vidaza, Mylosar
Ladakamycin(formerly), Azacitidine, U-18496, NSC-102816, Vidaza, Mylosar
阿扎胞苷Chemical Name: 5-Azacytidine; 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; 1-(beta-D-Ribofuranosyl)-5-azacytosine
CAS No. 320-67-2
项目整合开发状态: Launched-2004
项目研究机构: Pharmion (Orphan Drug), Pfizer (Originator), Pharmion (Licensee)
合成路线:The reaction of 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose (I) with dry HCl in ether-acetic anhydride gives 1-chloro-2,3,5-tri-O-acetyl-beta-D-ribofuranose (II),which by reaction with silver isocyanate in dry xylene is converted into 2,3,5-tri-O-acetyl-beta-D-ribofuranosylisocyanate (III).The reaction of (III) with 2-methylisourea (IV) in dry CHCl3 affords 1-(2,3,5-tri-O-acetyl-3-D-ribofuranosyl)-4-methylisobiuret (V),which is cyclized by reaction with ethyl orthoformate at 135 C yielding 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-4-methoxy-2-oxo-1,2-dihydro-1,3,5-triazine (VI).Finally,this compound is treated with ammonia in dry methanol.
📌 参考资料/链接：
参考文献标题:Nucleic acid components and their analogues.LI.Synthesis of 1-glycosyl derivatives of 5-azauracil and 5-azacytosine
文献作者:Sorm,F.; Piskala,A.
参考来源:Coll Czech Chem Commun 1964,292060-76
📄 详细内容
合成路线:The reaction of 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose (I) with dry HCl in ether-acetic anhydride gives 1-chloro-2,3,5-tri-O-acetyl-beta-D-ribofuranose (II),which by reaction with silver isocyanate in dry xylene is converted into 2,3,5-tri-O-acetyl-beta-D-ribofuranosylisocyanate (III).The reaction of (III) with 2-methylisourea (IV) in dry CHCl3 affords 1-(2,3,5-tri-O-acetyl-3-D-ribofuranosyl)-4-methylisobiuret (V),which is cyclized by reaction with ethyl orthoformate at 135 C yielding 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-4-methoxy-2-oxo-1,2-dihydro-1,3,5-triazine (VI).Finally,this compound is treated with ammonia in dry methanol.
参考文献标题:Azacitidine
文献作者:Von Hoff,D.D.
参考来源:Drugs Fut 1980,5(8),392
产品链接: CAS No. 320-67-2››