(1S,2R,4R)-1-benzoyloxy-2-(benzoyloxy)methyl-4-[N-(9-phenyl-9-fluorenyl)amino]cyclopentane | 493039-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (1S,2R,4R)-1-benzoyloxy-2-(benzoyloxy)methyl-4-[N-(9-phenyl-9-fluorenyl)amino]cyclopentane
• 英文别名: [(1R,2S,4R)-2-benzoyloxy-4-[(9-phenylfluoren-9-yl)amino]cyclopentyl]methyl benzoate
• CAS: 493039-12-6
• 化学式: C₃₉H₃₃NO₄
• 分子量: 579.695
• InChiKey: HFAKZLJIGQXQRV-NCCKSDQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,4R)-1-benzoyloxy-2-(benzoyloxy)methyl-4-[N-(9-phenyl-9-fluorenyl)amino]cyclopentane 在 10percent Pd/C 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 12.0h， 以95%的产率得到(1S,2R,4R)-4-amino-1-benzoyloxy-2-(benzoyloxymethyl)cyclopentane
  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：

  methyl (4S)-4-[N-(9-phenyl-9-fluorenyl)amino]-1-cyclopentenecarboxylate 在 吡啶 、 lithium aluminium tetrahydride 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 68.0h， 生成 (1S,2R,4R)-1-benzoyloxy-2-(benzoyloxy)methyl-4-[N-(9-phenyl-9-fluorenyl)amino]cyclopentane
  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.