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新产品编号:1302495

Chemical Name: 7-O-(4'-O-Acetyl-2',3',6'-trideoxy-3'-iodo-alpha-L-mannopyranosyl)daunomycinone
项目整合开发状态: Biological Testing
项目研究机构: Servier (Originator)
合成路线:Reduction of ketone (I) with NaBH4 in MeOH at low temperature yielded alcohol (II) as the major product.This was treated with trifluoromethanesulfonic anhydride to provide triflate (III),which was displaced with NaI to form iodide (IV).Acetolysis of the methyl pyranoside (IV) produced the 1-alpha-O-acetyl derivative (V) along with minor amounts of the beta-anomer.The reaction of (V) with dry HCl in benzene gave the corresponding glycosyl chloride,which was subsequently coupled with daunorubicinone (VI) using HgO and HgBr2 to provide the title compound as the major anomer.
📌 参考资料/链接:
参考文献标题:Design,synthesis and biological activity of 7-O-(4-O-acetyl-3-iodo-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)daunomycinone and 7-O-(3-chloro-2,3,6-trideoxy-4-O-propanoyl-alpha-L-lyxo-hexopyranosyl)daunomycinone
文献作者:Aligiannis,N.; Pouli,N.; Marakos,P.; Mitaku,S.; Skaltsounis,A.L.; Leonce,S.; Pierre,A.; Atassi,G.
参考来源:Chem Pharm Bull 2000,48(1),150