(2S,4R)-2-hydroxy-4-iodomethyl-4-butanolide | 830334-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S,4R)-2-hydroxy-4-iodomethyl-4-butanolide
• CAS: 830334-89-9
• 化学式: C₅H₇IO₃
• 分子量: 242.013
• InChiKey: GELOJDUISUSKMG-DMTCNVIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-2-hydroxy-4-iodomethyl-4-butanolide 在 silver(I) nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以46%的产率得到(3S,5S)-(+)-3-hydroxy-5-hydroxymethyl-tetrahydrofuran-2-one
  参考文献：
  名称：

  Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide

  摘要：

  The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide 13 is presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.025
• 作为产物：
  描述：

  N-((14S)-14-hydroxy-14-allyl)acetyloyl-(2R)-bornane-10,2-sultam 在 phosphate buffer 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以89%的产率得到(2R)-bornane-10,2-sultam
  参考文献：
  名称：

  Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide

  摘要：

  The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide 13 is presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.025