发明授权
US4357466A Processes for the production of 3'-deoxykanamycin A and intermediates
失效
制备3'-脱氧卡那霉素A和中间体的方法
- 专利标题: Processes for the production of 3'-deoxykanamycin A and intermediates
- 专利标题(中): 制备3'-脱氧卡那霉素A和中间体的方法
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申请号: US198612申请日: 1980-10-20
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公开(公告)号: US4357466A公开(公告)日: 1982-11-02
- 发明人: Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Tomo Jikihara
- 申请人: Hamao Umezawa , Sumio Umezawa , Tsutomu Tsuchiya , Tomo Jikihara
- 申请人地址: JPX Tokyo
- 专利权人: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
- 当前专利权人: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
- 当前专利权人地址: JPX Tokyo
- 优先权: JPX54-139798 19791031
- 主分类号: C07H15/234
- IPC分类号: C07H15/234 ; C07H15/236 ; A61K31/71 ; C07H15/22
摘要:
3'-Deoxykanamycin A useful as antibacterial agent is produced from a protected kanamycin A derivative either by a process comprising imidazolylthiocarbonylation of the 3'- and 2"-hydroxyl groups of 4",6"-O-cyclohexylidene-4'-0:6'-N-carbonyl-5,2'-O-isopropylidene-1,3,3"-tri-N-tosylkanamycin A, preferential removal of the 3'-imidazolylthiocarbonyloxy group with tributyltin hydride for the 3'-deoxygenation, followed by removal of the 2"-O-imidazolylthiocarbonyl group with aqueous ammonia, removal of the N-tosyl groups with alkali or alkaline earth metal in liquid ammonia, hydrolytic fission of the 4',6'-cyclic carbamate ring and concurrent removal of the 5,2'-O-isopropylidene group and 4",6"-O-cyclohexylidene group, or by a process comprising selective acetylation of the 2"-hydroxyl group of said protected kanamycin A derivative with acetyl chloride in pyridine, trifluoromethanesulfonylation of the 3'-hydroxyl group, followed by concurrent removal of the 3'-trifluoromethanesulfonyloxy group and N-tosyl groups with alkali metal in liquid ammonia, removal of the 2"-O-acetyl group concurrently with hydrolytic fission of 4',6'-cyclic carbamate, and hydrolytic removal of the 5,2'-O-isopropylidene and 4",6"-O-cyclohexylidene groups.
公开/授权文献
- US5466013A Card intermediate and method 公开/授权日:1995-11-14
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