ME-2303, FAD-104

Chemical Name: 7-O-(2,6-Dideoxy-2-fluoro-alpha-L-talopyranosyl)pimelyladryamycinone; (8S,10S)-8-(6-Carboxyhexanoyloxyacetyl)-10-[(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione; 7-O-(2,6-Dideoxy-2-fluoro-alpha-L-talopyranosyl)adriamycinone-14-O-hemipimelate
CAS No. 116521-53-0
项目整合开发状态: Phase II
项目研究机构: Meiji Seika (Originator)
合成路线:The condensation of (XII) with monosodium pimelate (XIII) in acetone - water yields the protected hemipimelate (XIV),which is finally treated with hot acetic acid - water.
📌 参考资料/链接:
参考文献标题:Novel anthracycline derivs.,a process for preparing them and their use as medicaments
文献作者:Umezawa,H.; Umezawa,S.; Tsuchiya,T.; Takeuchi,T.; Takagi,Y.; Yoneda,T.; Fukatsu,S.(Microbial Chemistry Research Foundation)
参考来源:EP 0275431; JP 1988141992

📄 详细内容


合成路线:The condensation of (XII) with monosodium pimelate (XIII) in acetone - water yields the protected hemipimelate (XIV),which is finally treated with hot acetic acid - water.

参考文献标题:Synthesis and antitumor activities of 14-O-acyl derivatives of 7-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl)adriamycin
文献作者:Tsuchiya,T.; Takagi,Y.; Umezawa,S.; Takeuchi,T.; Komuro,K.; Nosaka,C.; Umezawa,H.; Fukatsu,S.; Yoneta,T.
参考来源:J Antibiot 1988,41(7),988-91


合成路线:L-Fucose (I) is converted successively to its methyl glucoside (II),the 3,4-O-isopropylidene derivative (III),the 2-O-acetyl derivative (IV),the 2-O-acetyl-L-methylfucoside (V),the tosylate (VI),the 4-O-benzyl derivative (VII) and finally,through various steps,the 3,4-O-diacetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide (VIII).The condensation of (VIII) with daunomycinone (IX) gives the daunomycin derivative (X),which is converted to the isopropylidene derivative (XI).The bromination of (XI) affords the bromo derivative (XII).

合成路线:The condensation of (XII) with monosodium pimelate (XIII) in acetone - water yields the protected hemipimelate (XIV),which is finally treated with hot acetic acid - water.

参考文献标题:Biological properties of ME2303 (FAD-104),a new anthracycline
文献作者:Omoto,S.; Kondo,S.; Fukatsu,S.; Takeuchi,T.; Umezawa,K.; Tsuchiya,T.; Umezawa,S.
参考来源:Drug Exp Clin Res 1988,14(7),435-9


合成路线:L-Fucose (I) is converted successively to its methyl glucoside (II),the 3,4-O-isopropylidene derivative (III),the 2-O-acetyl derivative (IV),the 2-O-acetyl-L-methylfucoside (V),the tosylate (VI),the 4-O-benzyl derivative (VII) and finally,through various steps,the 3,4-O-diacetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide (VIII).The condensation of (VIII) with daunomycinone (IX) gives the daunomycin derivative (X),which is converted to the isopropylidene derivative (XI).The bromination of (XI) affords the bromo derivative (XII).

合成路线:The condensation of (XII) with monosodium pimelate (XIII) in acetone - water yields the protected hemipimelate (XIV),which is finally treated with hot acetic acid - water.
参考文献标题:ME2303
文献作者:Hoshi,A.; Prous,J.; Castar,J.
参考来源:Drugs Fut 1989,14(8),756


产品链接: CAS No. 116521-53-0››