Welcome乐天彩票app下载为梦而年轻!

  •  
高级搜索 标王直达
 
 
当前位置: 乐天彩票app下载 » 资料 » 医药中间体库 » ,C18H21NO5,331.3718,4-methyl 3-(phenylmethyl) octahydro-3H-o

,C18H21NO5,331.3718,4-methyl 3-(phenylmethyl) octahydro-3H-o

放大字体  缩小字体 更新日期:2018-11-23  浏览次数:134
摘 要:,C18H21NO5,331.3718,4-methyl 3-(phenylmethyl) octahydro-3H-oxireno[2,3-f]indole-3,4-dicarboxylate
  • 【化学名】4-methyl 3-(phenylmethyl) octahydro-3H-oxireno[2,3-f]indole-3,4-dicarboxylate
  • 【CAS登记号】
  • 【结构式】,C18H21NO5,331.3718,4-methyl 3-(phenylmethyl) octahydro-3H-o--药物合成数据库
  • 【分子式】C18H21NO5
  • 【分子量】331.3718
  • 【来源】
  • 【合成情况】 
  • 〖目标产物〗Dysinosin A
  • 〖合成路线〗
  • 〖合成方法〗Synthesis of the perhydroindole intermediate (XIII): The alkylation of the N-protected glutamate (I) with allyl bromide (II) by means of LiHMDS in THF gives the protected chiral allyl glutamate (III) (1), which is cyclized by means of TFA in dichloromethane to yield the pyroglutamate (IV). The reduction of (IV) with LiHBEt3 in THF affords the hydroxy compound (V), which is treated with Ac2O and DMAP in dichloromethane to provide the expected hemiaminal derivative (VI). The reaction of (VI) with allyl tributylstannane (VII) by means of BF3/Et2O in toluene gives the diallyl pyrrolidine (VIII), which is submitted to a ring closure by olefin metathesis using a Grubbs Ru catalyst in dichloromethane to yield the hexahydroindole derivative (IX). The reaction of (IX) with mCPBA in dichloromethane affords the epoxide (X), which is hydrolyzed with TFA to yield the dihydroxy compound (XI). The reaction of (XI) with Mom-Cl and DIEA in dichloromethane provides the bis mom ether (XII), which is treated with H2 over Pd/C in methanol to yield the desired perhydroindole intermediate (XIII) (2).
  • 〖参考〗Hanessian, S.; Margarita, R.; Hall, A.; Johnstone, S.; Tremblay, M.; Parlanti, L.; Total synthesis and structural confirmation of the marine natural product Dysinosin A: A novel inhibitor of thrombin and Factor VIIa. J Am Chem Soc 2002, 124, 45, 13342
  • 〖目标产物〗Dysinosin A
  • 〖合成路线〗
  • 〖合成方法〗Synthesis of the perhydroindole intermediate (XIII): The alkylation of the N-protected glutamate (I) with allyl bromide (II) by means of LiHMDS in THF gives the protected chiral allyl glutamate (III) (1), which is cyclized by means of TFA in dichloromethane to yield the pyroglutamate (IV). The reduction of (IV) with LiHBEt3 in THF affords the hydroxy compound (V), which is treated with Ac2O and DMAP in dichloromethane to provide the expected hemiaminal derivative (VI). The reaction of (VI) with allyl tributylstannane (VII) by means of BF3/Et2O in toluene gives the diallyl pyrrolidine (VIII), which is submitted to a ring closure by olefin metathesis using a Grubbs Ru catalyst in dichloromethane to yield the hexahydroindole derivative (IX). The reaction of (IX) with mCPBA in dichloromethane affords the epoxide (X), which is hydrolyzed with TFA to yield the dihydroxy compound (XI). The reaction of (XI) with Mom-Cl and DIEA in dichloromethane provides the bis mom ether (XII), which is treated with H2 over Pd/C in methanol to yield the desired perhydroindole intermediate (XIII) (2).
  • 〖参考〗Hanessian, S.; Margarita, R.; 1,3-Asymmetric induction in dianionic allylation reactions of amino acid derivatives-synthesis of functionally useful enantiopure glutamates, pipecolates and pyroglutamates. Tetrahedron Lett 1998, 39, 33, 5887
 
本文导航:
  • (1) ,C18H21NO5,331.3718,4-methyl 3-(phenylmethyl) octahydro-3H-o
  • 下一篇:鳖甲
  • 上一篇:暂无
 
[ 资料搜索 ]  [ 加入收藏 ]  [ 告诉好友 ]  [ 打印本文 ]  [ 关闭窗口 ]

 

 
推荐图文
推荐资料
热门关注
 
乐天彩票app下载 | 关于乐天彩票app下载 | 联系方式 | 使用协议 | 网站地图 | 排名推广 | 广告服务 | 会员服务 | RSS订阅
CopyRight© 2004-2018 taose8.com All Rights Reserved. 更新时间:2018-11-23 18:21
版权所有 药品资讯网www.taose8.com
增值电信业务经营许可证:  互联网药品信息服务资格证书: 
平安网站