methyl (3S)-3-[N-(9-phenyl-9-fluorenyl)amino]-4-oxobutanoate | 493039-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl (3S)-3-[N-(9-phenyl-9-fluorenyl)amino]-4-oxobutanoate
• 英文别名: methyl (3S)-4-oxo-3-[(9-phenylfluoren-9-yl)amino]butanoate
• CAS: 493039-02-4
• 化学式: C₂₄H₂₁NO₃
• 分子量: 371.436
• InChiKey: BJIVRBOWHZXEJA-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三甲基膦酰基乙酸酯 、 methyl (3S)-3-[N-(9-phenyl-9-fluorenyl)amino]-4-oxobutanoate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 methyl (3S)-5-methoxycarbonyl-3-[N-(9-phenyl-9-fluorenyl)amino]-4(Z)-pentenoate 、 methyl (3S)-5-methoxycarbonyl-3-[N-(9-phenyl-9-fluorenyl)amino]-4(E)-pentenoate
  参考文献：
  名称：

  Enantiospecific Synthesis of Carbapentostatins

  摘要：

  In this paper we describe enantioselective syntheses of (+)-carbapentostatin (8) and its cyclopentyl analogue 12b. A new and efficient one-pot, two-step preparation of aldehyde 15 has been developed, based on the borane reduction of N-Pf-protected L-aspartic acid gamma-methyl ester (13) and Swern, oxidation of the resulting alcohol. Homologation to diester 18 and ring formation by Dieckman cyclization, followed by reduction and dehydration steps, afford the 4-amino-1-cyclopentenemethanol derivative 22. Hydroboration and oxidation transform this compound stereospecifically into aminocyclopentanol 26, the key aminocyclitol component for an asymmetric synthesis of (+)carbapentostatin.

  DOI：

  10.1021/jo020612x
• 作为产物：
  描述：

  (S)-4-methoxy-4-oxo-2-((9-phenyl-9H-fluoren-9-yl)amino)butanoic acid 在 草酰氯 、 硼烷 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 60.5h， 生成 methyl (3S)-3-[N-(9-phenyl-9-fluorenyl)amino]-4-oxobutanoate
  参考文献：
  名称：

  Enantiospecific Synthesis of Carbapentostatins

  摘要：

  In this paper we describe enantioselective syntheses of (+)-carbapentostatin (8) and its cyclopentyl analogue 12b. A new and efficient one-pot, two-step preparation of aldehyde 15 has been developed, based on the borane reduction of N-Pf-protected L-aspartic acid gamma-methyl ester (13) and Swern, oxidation of the resulting alcohol. Homologation to diester 18 and ring formation by Dieckman cyclization, followed by reduction and dehydration steps, afford the 4-amino-1-cyclopentenemethanol derivative 22. Hydroboration and oxidation transform this compound stereospecifically into aminocyclopentanol 26, the key aminocyclitol component for an asymmetric synthesis of (+)carbapentostatin.

  DOI：

  10.1021/jo020612x

文献信息

• Enantiospecific Synthesis of Carbapentostatins
  作者：Jonathan Z. Ho、Rafat M. Mohareb、Jin Hee Ahn、Tae Bo Sim、Henry Rapoport

  DOI：10.1021/jo020612x

  日期：2003.1.1

  In this paper we describe enantioselective syntheses of (+)-carbapentostatin (8) and its cyclopentyl analogue 12b. A new and efficient one-pot, two-step preparation of aldehyde 15 has been developed, based on the borane reduction of N-Pf-protected L-aspartic acid gamma-methyl ester (13) and Swern, oxidation of the resulting alcohol. Homologation to diester 18 and ring formation by Dieckman cyclization, followed by reduction and dehydration steps, afford the 4-amino-1-cyclopentenemethanol derivative 22. Hydroboration and oxidation transform this compound stereospecifically into aminocyclopentanol 26, the key aminocyclitol component for an asymmetric synthesis of (+)carbapentostatin.