(2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine | 158177-64-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine
• 英文别名: tert-butyl (2S,3R,4R)-1-benzoyl-4-hydroxy-4-(4-methoxyphenyl)-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]pyrrolidine-2-carboxylate
• CAS: 158177-64-1
• 化学式: C₂₉H₃₇NO₇
• 分子量: 511.615
• InChiKey: GZPHBMNVGWRTOR-VTYUZOFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine 在 三氟乙酸 作用下， 反应 12.0h， 以100%的产率得到6-benzoyl-2-oxo-8(S)-(4-methoxyphenyl)-6-aza-1-oxa-4(R)-bicyclo <3.3.0> octane-5(S)-carboxylic acid
  参考文献：
  名称：

  迈向通用的类胡萝卜素合成：建立C-4立体化学的两种方法

  摘要：

  苯甲酸内酯的氢解和酰胺还原反应被用于生成被保护的C-4芳基取代的类海因类似物，该类似物被去保护成其相应的游离氨基酸。获得了C-4 2-MeOPh-类似物的X射线晶体学数据。

  DOI：

  10.1016/s0040-4020(97)00191-9
• 作为产物：
  描述：

  N-benzoyl-4-oxo-L-proline tert-butyl ester 在 5A molecular sieve 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醚 、 苯 为溶剂， 反应 168.0h， 生成 (2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine
  参考文献：
  名称：

  Towards a versatile synthesis of kainoids I: Introduction of the C-3 and C-4 substituents

  摘要：

  The first stages in the synthesis of acromelic acid analogues from trans-4-hydroxy-L-proline are described. An enamine alkylation was used to stereospecifically introduce the C-3 substituent, Grignard addition to a ketone or Pd(0) catalysed cross-coupling procedures adding C-4 aryl substituents for further manipulation. A number of versatile intermediates were generated. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00190-7

文献信息

• Towards a versatile synthesis of kainoids I: Introduction of the C-3 and C-4 substituents
  作者：Jack E. Baldwin、Samantha J. Bamford、Andrew M. Fryer、Martin P.W. Rudolph、Mark E. Wood

  DOI：10.1016/s0040-4020(97)00190-7

  日期：1997.4

  The first stages in the synthesis of acromelic acid analogues from trans-4-hydroxy-L-proline are described. An enamine alkylation was used to stereospecifically introduce the C-3 substituent, Grignard addition to a ketone or Pd(0) catalysed cross-coupling procedures adding C-4 aryl substituents for further manipulation. A number of versatile intermediates were generated. (C) 1997 Elsevier Science Ltd.
• Towards a versatile synthesis of kainoids II: Two methods for establishment of C-4 stereochemistry
  作者：Jack E. Baldwin、Samantha J. Bamford、Andrew M. Fryer、Martin P.W. Rudolph、Mark E. Wood

  DOI：10.1016/s0040-4020(97)00191-9

  日期：1997.4

  Benzylic lactone hydrogenolysis and enamide reduction were used to generate protected C-4 aryl substituted kainoid analogues which were deprotected to their corresponding free amino acids. X-ray crystographic data were obtained for the C-4 2-MeOPh- analogue.

  苯甲酸内酯的氢解和酰胺还原反应被用于生成被保护的C-4芳基取代的类海因类似物，该类似物被去保护成其相应的游离氨基酸。获得了C-4 2-MeOPh-类似物的X射线晶体学数据。