(5S)-5-[3-(2-hydroxyethylsulfonyl)-5-methoxy-4-propoxyphenyl]oxolan-2-one | 140705-19-7

• 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: (5S)-5-[3-(2-hydroxyethylsulfonyl)-5-methoxy-4-propoxyphenyl]oxolan-2-one
• CAS: 140705-19-7
• 化学式: C₁₆H₂₂O₇S
• 分子量: 358.412
• InChiKey: GQCZQWRSCUZKKZ-LBPRGKRZSA-N

物化性质

• 沸点：
  625.4±55.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5S)-5-[3-(2-hydroxyethylsulfonyl)-5-methoxy-4-propoxyphenyl]oxolan-2-one 在 咪唑 、 三甲基溴硅烷 、 草酸 、 二异丁基氢化铝 、 magnesium 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷-D2 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.0h， 生成 2-[3-甲氧基-2-丙氧基-5-[(2S,5S)-5-(3,4,5-三甲氧基苯基)四氢呋喃-2-基]苯基]磺酰基乙醇
  参考文献：
  名称：

  Synthesis of PAF antagonist MK-287

  摘要：

  The synthesis of PAF antagonist MK-287 is described. Our route utilizes a 5-aryl-substituted butyrolactone as the key optically active intermediate, which is constructed in four steps from commercially available 5-iodovanillin. Asymmetry is introduced using beta-chlorodiisopinocampheylborane to reduce a prochiral ketone. The second asymmetric center is installed relative to the existing stereocenter with stereocontrol exceeding 50:1. This step utilizes a copper-catalyzed Grignard displacement of an alpha-bromo ether. The alpha-bromo ether was generated using trimethylsilyl bromide activation of a silylated hemiacetal. The details leading to our development of the silyl acetal method for anomeric activation are also described.

  DOI：

  10.1021/jo00052a013
• 作为产物：
  描述：

  N-(9,10,15,18,20,21-六氢-5,10,15,18,21-五羰基-5H-萘并[2,3-h]萘并[2',3':6,7]吲哚并[2,3-b]吖啶-4-基)苯酰胺 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以95%的产率得到(5S)-5-[3-(2-hydroxyethylsulfonyl)-5-methoxy-4-propoxyphenyl]oxolan-2-one
  参考文献：
  名称：

  Synthesis of PAF antagonist MK-287

  摘要：

  The synthesis of PAF antagonist MK-287 is described. Our route utilizes a 5-aryl-substituted butyrolactone as the key optically active intermediate, which is constructed in four steps from commercially available 5-iodovanillin. Asymmetry is introduced using beta-chlorodiisopinocampheylborane to reduce a prochiral ketone. The second asymmetric center is installed relative to the existing stereocenter with stereocontrol exceeding 50:1. This step utilizes a copper-catalyzed Grignard displacement of an alpha-bromo ether. The alpha-bromo ether was generated using trimethylsilyl bromide activation of a silylated hemiacetal. The details leading to our development of the silyl acetal method for anomeric activation are also described.

  DOI：

  10.1021/jo00052a013

文献信息

• Thompson Andrew S., Tschaen David M., Simpson Pamela, McSwine Donna J., R+, J. Org. Chem., 57 (1992) N 26, S 7044-7052
  作者：Thompson Andrew S., Tschaen David M., Simpson Pamela, McSwine Donna J., R+

  DOI：——

  日期：——
• Synthesis of PAF antagonist MK-287
  作者：Andrew S. Thompson、David M. Tschaen、Pamela Simpson、Donna J. McSwine、Robert A. Reamer、Thomas R. Verhoeven、Ichiro Shinkai

  DOI：10.1021/jo00052a013

  日期：1992.12

  The synthesis of PAF antagonist MK-287 is described. Our route utilizes a 5-aryl-substituted butyrolactone as the key optically active intermediate, which is constructed in four steps from commercially available 5-iodovanillin. Asymmetry is introduced using beta-chlorodiisopinocampheylborane to reduce a prochiral ketone. The second asymmetric center is installed relative to the existing stereocenter with stereocontrol exceeding 50:1. This step utilizes a copper-catalyzed Grignard displacement of an alpha-bromo ether. The alpha-bromo ether was generated using trimethylsilyl bromide activation of a silylated hemiacetal. The details leading to our development of the silyl acetal method for anomeric activation are also described.