(4S,5R)-4-hydroxy-5-hydroxymethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester | 366450-24-0

• 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-hydroxymethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,3S)-3-hydroxy-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate
• CAS: 366450-24-0
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: WWWJBJGKIWXDIW-RQJHMYQMSA-N

物化性质

• 沸点：
  426.8±30.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-hydroxy-5-hydroxymethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 吡啶 、 氢气 、 碳酸氢钠 、 sodium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-Boc-4-hydroxy-5-methyl-pyrrolidin-2-one
  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
• 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 盐酸 作用下， 以100%的产率得到(4S,5R)-4-hydroxy-5-hydroxymethyl-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.