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CAS 1443528-80-0

tert-Butyl [(3S,5R,6R)-5,6-dihydroxy-2-oxopiperidin-3-yl]carbamate

登记编号:ANID-024、(V)796686-1-a

应用背景(按来源药适应症)

念珠菌病阿尼芬净念珠菌血症阿尼芬净真菌感染阿尼芬净腹膜炎阿尼芬净脓肿阿尼芬净呼吸道感染阿尼芬净侵袭性念珠菌病醋酸瑞扎芬净念珠菌病醋酸瑞扎芬净念珠菌血症醋酸瑞扎芬净卡氏肺囊虫感染醋酸瑞扎芬净侵袭性真菌感染醋酸瑞扎芬净曲霉菌属感染醋酸瑞扎芬净

来源药(使用该中间体的合成路线)

品种梯队到期年
阿尼芬净AnidulafunginTier C · 观察 / 贸易-
醋酸瑞扎芬净Rezafungin acetateTier C · 观察 / 贸易-

合成路线中的位置(上下游链)

按路线登记顺序排列,左→右为合成方向;高亮为当前 CAS,其余可点击跳转对应档案。

阿尼芬净优化路线步数:9总收率:/
(S)-N-Boc-allylglycine→Allylamine→tert-Butyl [(2S)-1-oxo-1-[(prop-2-en-1-yl)amino]pent-4-en-2-yl]carbamate→tert-Butyl [(3S)-2-oxo-1,2,3,4-tetrahydropyridin-3-yl]carbamate→tert-Butyl [(3S,5R,6R)-5,6-dihydroxy-2-oxopiperidin-3-yl]carbamate→(4R,5R)-N2-(tert-Butoxycarbonyl)-4,5-dihydroxy-L-ornithine→(4R,5R)-N2-(tert-Butoxycarbonyl)-N5-[[(9H-fluoren-9-yl)oxy]carbonyl]-4,5-dihydroxy-L-ornithine→(4R,5R)-4,5-Bis(acetyloxy)-N2-(tert-butoxycarbonyl)-N5-[[(9H-fluoren-9-yl)oxy]carbonyl]-L-ornithine→Resin bound (4R,5R)-4,5-bis(acetyloxy)-N2-(tert-butoxycarbonyl)-N5-[[(9H-fluoren-9-yl)oxy]carbonyl]-L-ornithine→(3S,4S)-N-Fmoc-3-acetoxy-4-methyl-L-proline→Resin bound N5-[(3S,4S)-3-(acetyloxy)-1-[[(9H-fluoren-9-yl)oxy]carbonyl]-4-methyl-L-prolyl]-(4R,5R)-4,5-bis(acetyloxy)-N2-(tert-butoxycarbonyl)-L-ornithine→O-Acetyl-N-[[(9H-fluoren-9-yl)oxy]carbonyl]-L-threonine→Resin bound N5-[O-acetyl-N-[[(9H-fluoren-9-yl)oxy]carbonyl]-L-threonyl-(3S,4S)-3-(acetyloxy)-4-methyl-L-prolyl]-(4R,5R)-4,5-bis(acetyloxy)-N2-(tert-butoxycarbonyl)-L-ornithine
醋酸瑞扎芬净优化路线步数:9总收率:/
(S)-N-Boc-allylglycine→Allylamine→tert-Butyl [(2S)-1-oxo-1-[(prop-2-en-1-yl)amino]pent-4-en-2-yl]carbamate→tert-Butyl [(3S)-2-oxo-1,2,3,4-tetrahydropyridin-3-yl]carbamate→tert-Butyl [(3S,5R,6R)-5,6-dihydroxy-2-oxopiperidin-3-yl]carbamate→(4R,5R)-N2-(tert-Butoxycarbonyl)-4,5-dihydroxy-L-ornithine→(4R,5R)-N2-(tert-Butoxycarbonyl)-N5-[[(9H-fluoren-9-yl)oxy]carbonyl]-4,5-dihydroxy-L-ornithine→(4R,5R)-4,5-Bis(acetyloxy)-N2-(tert-butoxycarbonyl)-N5-[[(9H-fluoren-9-yl)oxy]carbonyl]-L-ornithine→Resin bound (4R,5R)-4,5-bis(acetyloxy)-N2-(tert-butoxycarbonyl)-N5-[[(9H-fluoren-9-yl)oxy]carbonyl]-L-ornithine→(3S,4S)-N-Fmoc-3-acetoxy-4-methyl-L-proline→Resin bound N5-[(3S,4S)-3-(acetyloxy)-1-[[(9H-fluoren-9-yl)oxy]carbonyl]-4-methyl-L-prolyl]-(4R,5R)-4,5-bis(acetyloxy)-N2-(tert-butoxycarbonyl)-L-ornithine→O-Acetyl-N-[[(9H-fluoren-9-yl)oxy]carbonyl]-L-threonine→Resin bound N5-[O-acetyl-N-[[(9H-fluoren-9-yl)oxy]carbonyl]-L-threonyl-(3S,4S)-3-(acetyloxy)-4-methyl-L-prolyl]-(4R,5R)-4,5-bis(acetyloxy)-N2-(tert-butoxycarbonyl)-L-ornithine→3(4)-(Pentyloxy)-N-[(2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-2,11,12,15-tetrahydroxy-6,20-bis[(1R)-1-hydroxyethyl]-23-[(4S,5S)-5-(4-hydroxyphenyl)-2-phenyl-1,3,2-dioxaborolan-4-yl]-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl][1(1),2(1):2(4),3(1)-terphenyl]-1(4)-carboxamide

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