Di-tert-butyl (4-(benzyloxy)-(S)-2-(tosyloxy)butyl)malonate | 161111-10-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Di-tert-butyl (4-(benzyloxy)-(S)-2-(tosyloxy)butyl)malonate
• 英文别名: ditert-butyl 2-[(2S)-2-(4-methylphenyl)sulfonyloxy-4-phenylmethoxybutyl]propanedioate
• CAS: 161111-10-0
• 化学式: C₂₉H₄₀O₈S
• 分子量: 548.698
• InChiKey: XAJYFMFAYLMMAD-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Di-tert-butyl (4-(benzyloxy)-(S)-2-(tosyloxy)butyl)malonate 在 palladium on activated charcoal TEA 、 氢气 、 双(三甲基硅烷基)氨基钾 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 1.17h， 生成 ethoxycarbonyl (1S,6R)-2-oxo-3-oxabicyclo[4.1.0]heptane-1-carboxylate
  参考文献：
  名称：

  Synthesis of (1R,3R,5S)-1-Amino-3-(hydroxymethyl)bicyclo[3.1.0]hexane as a Precursor for the Synthesis of Carbocyclic Nucleosides

  摘要：

  The stereocontrolled synthesis has been achieved of a 1,5-methano-1-amino-5-(hydroxymethyl)cyclopentane, a potential component for carbocyclic nucleosides. Stereocontrol was manifest by converting (R)-2-((benzyloxy)ethyl)oxirane specifically to (2S,3S)-2-amino-2,3-methanoadipate through a series of lactones. This aminocyclopropanecarboxylate was then cyclized to the corresponding cyclopentanone ester. Reduction of the ketone, elimination, and hydrogenation of the double bond led primarily to the cyclopentane with the amino and ester groups trans (9/1). Enolization followed by an ammonium chloride quench then inverted this to a mixture in which the cis isomer was dominant(4/1). Simple functional group manipulation then gave the target (1R,3R,5S)-1-amino-3-(hydroxymethyl)bicyclo[3.1.0]hexane.

  DOI：

  10.1021/jo00097a040
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 Di-tert-butyl (4-(benzyloxy)-(S)-2-(tosyloxy)butyl)malonate
  参考文献：
  名称：

  Synthesis of (1R,3R,5S)-1-Amino-3-(hydroxymethyl)bicyclo[3.1.0]hexane as a Precursor for the Synthesis of Carbocyclic Nucleosides

  摘要：

  The stereocontrolled synthesis has been achieved of a 1,5-methano-1-amino-5-(hydroxymethyl)cyclopentane, a potential component for carbocyclic nucleosides. Stereocontrol was manifest by converting (R)-2-((benzyloxy)ethyl)oxirane specifically to (2S,3S)-2-amino-2,3-methanoadipate through a series of lactones. This aminocyclopropanecarboxylate was then cyclized to the corresponding cyclopentanone ester. Reduction of the ketone, elimination, and hydrogenation of the double bond led primarily to the cyclopentane with the amino and ester groups trans (9/1). Enolization followed by an ammonium chloride quench then inverted this to a mixture in which the cis isomer was dominant(4/1). Simple functional group manipulation then gave the target (1R,3R,5S)-1-amino-3-(hydroxymethyl)bicyclo[3.1.0]hexane.

  DOI：

  10.1021/jo00097a040

文献信息

• Synthesis of (1R,3R,5S)-1-Amino-3-(hydroxymethyl)bicyclo[3.1.0]hexane as a Precursor for the Synthesis of Carbocyclic Nucleosides
  作者：Hae Sung Chang、Stephen C. Bergmeier、Jeffrey A. Frick、Andreas Bathe、Henry Rapoport

  DOI：10.1021/jo00097a040

  日期：1994.9

  The stereocontrolled synthesis has been achieved of a 1,5-methano-1-amino-5-(hydroxymethyl)cyclopentane, a potential component for carbocyclic nucleosides. Stereocontrol was manifest by converting (R)-2-((benzyloxy)ethyl)oxirane specifically to (2S,3S)-2-amino-2,3-methanoadipate through a series of lactones. This aminocyclopropanecarboxylate was then cyclized to the corresponding cyclopentanone ester. Reduction of the ketone, elimination, and hydrogenation of the double bond led primarily to the cyclopentane with the amino and ester groups trans (9/1). Enolization followed by an ammonium chloride quench then inverted this to a mixture in which the cis isomer was dominant(4/1). Simple functional group manipulation then gave the target (1R,3R,5S)-1-amino-3-(hydroxymethyl)bicyclo[3.1.0]hexane.