(4S,5R)-4-hydroxy-5-methanesulfonyloxymethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester | 366450-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4S,5R)-4-hydroxy-5-methanesulfonyloxymethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,3S)-3-hydroxy-2-(methylsulfonyloxymethyl)-5-oxopyrrolidine-1-carboxylate
• CAS: 366450-25-1
• 化学式: C₁₁H₁₉NO₇S
• 分子量: 309.34
• InChiKey: NZVCVPRPESWPDW-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-hydroxy-5-methanesulfonyloxymethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 (2R,3S)-2-Aminomethyl-3-hydroxy-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective Formal Synthesis of Pseudodistomin C

  摘要：

  [GRAPHICS]Trisubstituted benzenesulfonylmethylpiperidine 4, in which the substituents are all cis to each other, is a direct synthetic precursor of the cytotoxic marine alkaloid pseudodistomin C; it has been synthesized with total diastereoselectivities from (S)-pyroglutaminol.

  DOI：

  10.1021/ol010221p
• 作为产物：
  描述：

  (2R,3S)-3-(1-Ethoxy-ethoxy)-2-(1-ethoxy-ethoxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 在 吡啶 、 盐酸 作用下， 生成 (4S,5R)-4-hydroxy-5-methanesulfonyloxymethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Diastereospecific formal synthesis of (2R,3S)-2-amino-tetradeca-5,7-dien-3-ol isolated from Xestospongia sp.

  摘要：

  Stereospecific synthesis of a common precursor of several acyclic (2R,3S)-2-amino-3-ols from marine origin, especially of (2R,3S)-2-amino-tetradeca-5,7-dien-3-ol isolated from Xestospongia sp., is described starting from the versatile epoxide 10. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01097-8

文献信息

• Stereoselective Formal Synthesis of Pseudodistomin C
  作者：Nicole Langlois

  DOI：10.1021/ol010221p

  日期：2002.1.1

  [GRAPHICS]Trisubstituted benzenesulfonylmethylpiperidine 4, in which the substituents are all cis to each other, is a direct synthetic precursor of the cytotoxic marine alkaloid pseudodistomin C; it has been synthesized with total diastereoselectivities from (S)-pyroglutaminol.
• Diastereospecific formal synthesis of (2R,3S)-2-amino-tetradeca-5,7-dien-3-ol isolated from Xestospongia sp.
  作者：Nicole Langlois

  DOI：10.1016/s0040-4039(01)01097-8

  日期：2001.8

  Stereospecific synthesis of a common precursor of several acyclic (2R,3S)-2-amino-3-ols from marine origin, especially of (2R,3S)-2-amino-tetradeca-5,7-dien-3-ol isolated from Xestospongia sp., is described starting from the versatile epoxide 10. (C) 2001 Elsevier Science Ltd. All rights reserved.