Caspofungin acetate, MK-0991, MK-991, L-743872, Caspofungin MSD, Cancidas
醋酸卡泊芬净 卡泊芬净 Chemical Name: (3S,6S,9S,11R,15S,18S,20R,21S,24S,25S)-21-(2-Aminoethylamino)-3-[3-amino-1(R)-hydroxypropyl]-6-[1(S),2(S)-dihydroxy-2-(4-hydroxyphenyl)ethyl]-18-(10,12-dimethyltetradecanamido)-11,20,25-trihydroxy-15-[1(R)-hydroxyethyl]-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0(9,13)]heptacosane-2,5,8,14,17,23-hexaone diacetate; (2R,6S,9S,11R,12S,14aS,15S,20S,23S,25aS)-12-(2-Aminoethylamino)-20-[3-amino-1(R)-hydroxypropyl]-23-[1(S),2(S)-dihydroxy-2-(4-hydroxyphenyl)ethyl]-9-(10,12-dimethyltetradecanamido)-2,11,15-trihydroxy-6-[1(R)-hydroxyethyl]perhydrodipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacycloheneicosine-5,8,14,19,22,25-hexaone diacetate; 1-[(4R,5S)-5-(2-Aminoethylamino)-N2-(10,12-dimethyl-1-oxotetradecyl)-4-hydroxy-L-ornithine]-5-[3(R)-hydroxy-L-ornithine]-pneumocandin B0 diacetate
CAS No. 179463-17-3, 162808-62-0 (free base)
项目整合开发状态: Launched-2001
项目研究机构: Merck & Co. (Originator)
合成路线:The reaction of cyclopeptide (V) with 2-sulfanylethylamine (VI) by means of camphorsulfonic acid (CSA) in DMF gives the epi-2-aminoethylsulfanyl compound (VII),which is oxidized with oxone in acetonitrile/water,affording the sulfone (VIII).Finally,this compound is treated with ethylenediamine in DMF to afford the target compound.
📌 参考资料/链接：
参考文献标题:Aza cyclohexapeptide cpds.
文献作者:Balkovec,J.M.; Bouffard,F.A.; Black,R.M.(Merck & Co.,Inc.)
参考来源:CA 2118757; EP 0620232; JP 1994321986; US 5378804; WO 9421677
📄 详细内容
合成路线:The reaction of cyclopeptide (I) with phenylboronic acid in THF gives the bis boronate (II),which is reduced at the carbamoyl group with BH3/S(Me)2 in THF and deprotected with HCl to afford the cyclopeptide (III).The reaction of (III) with thiophenol and TFA in acetonitrile affords the phenylsulfanyl derivative (IV),which is finally treated with ethylenediamine to afford the target compound.Alternatively,cyclopeptide (I) can be reduced directly to cyclopeptide (II) with BH3/S(Me)2 in THF.
参考文献标题:A process for preparing certain aza cyclohexapeptides
文献作者:Belyk,K.M.; Black,R.M.; Hugues,D.L.; Bender,D.R.; Leonard,W.(Merck & Co.,Inc.)
参考来源:WO 9624613
合成路线:The reaction of cyclopeptide (I) with phenylboronic acid in THF gives the bis boronate (II),which is reduced at the carbamoyl group with BH3/S(Me)2 in THF and deprotected with HCl to afford the cyclopeptide (III).The reaction of (III) with thiophenol and TFA in acetonitrile affords the phenylsulfanyl derivative (IV),which is finally treated with ethylenediamine to afford the target compound.Alternatively,cyclopeptide (I) can be reduced directly to cyclopeptide (II) with BH3/S(Me)2 in THF.
参考文献标题:Process for preparing certain aza cyclohexapeptides
文献作者:Hugues,D.L.; Belyk,K.M.; Black,R.M.; Bender,D.R.; Leonard,W.(Merck & Co.,Inc.)
参考来源:US 5552521
合成路线:The reaction of cyclopeptide (I) with phenylboronic acid in THF gives the bis boronate (II),which is reduced at the carbamoyl group with BH3/S(Me)2 in THF and deprotected with HCl to afford the cyclopeptide (III).The reaction of (III) with thiophenol and TFA in acetonitrile affords the phenylsulfanyl derivative (IV),which is finally treated with ethylenediamine to afford the target compound.Alternatively,cyclopeptide (I) can be reduced directly to cyclopeptide (II) with BH3/S(Me)2 in THF.
参考文献标题:A process for preparing certain aza cyclohexapeptides
文献作者:Leonard,W.; Belyk,K.M.(Merck & Co.,Inc.)
参考来源:WO 9747645
合成路线:The reaction of cyclopeptide (I) with phenylboronic acid in THF gives the bis boronate (II),which is reduced at the carbamoyl group with BH3/S(Me)2 in THF and deprotected with HCl to afford the cyclopeptide (III).The reaction of (III) with thiophenol and TFA in acetonitrile affords the phenylsulfanyl derivative (IV),which is finally treated with ethylenediamine to afford the target compound.Alternatively,cyclopeptide (I) can be reduced directly to cyclopeptide (II) with BH3/S(Me)2 in THF.
参考文献标题:Process for preparing certain aza cyclohexapeptides
文献作者:Leonard,W.; Belyk,K.M.(Merck & Co.,Inc.)
参考来源:US 5936062
合成路线:The reaction of cyclopeptide (I) with phenylboronic acid in THF gives the bis boronate (II),which is reduced at the carbamoyl group with BH3/S(Me)2 in THF and deprotected with HCl to afford the cyclopeptide (III).The reaction of (III) with thiophenol and TFA in acetonitrile affords the phenylsulfanyl derivative (IV),which is finally treated with ethylenediamine to afford the target compound.Alternatively,cyclopeptide (I) can be reduced directly to cyclopeptide (II) with BH3/S(Me)2 in THF.
参考文献标题:Antifungal compsns.
文献作者:Kaufman,M.J.; Hunke,W.A.; Neururkar,M.J.(Merck & Co.,Inc.)
参考来源:US 6136783
合成路线:The reaction of cyclopeptide (V) with 2-sulfanylethylamine (VI) by means of camphorsulfonic acid (CSA) in DMF gives the epi-2-aminoethylsulfanyl compound (VII),which is oxidized with oxone in acetonitrile/water,affording the sulfone (VIII).Finally,this compound is treated with ethylenediamine in DMF to afford the target compound.
参考文献标题:Aza cyclohexapeptide cpds.
文献作者:Balkovec,J.M.; Black,R.M.; Bouffard,F.A.(Merck & Co.,Inc.)
参考来源:US 5792746
产品链接: CAS No. 179463-17-3›› 产品链接: CAS No.162808-62-0››