(5S)-5-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-3-[(1R)-1-phenylethyl]-1,3-thiazolidin-4-one | 183183-39-3

• 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-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-3-[(1R)-1-phenylethyl]-1,3-thiazolidin-4-one
• CAS: 183183-39-3
• 化学式: C₂₆H₃₅NO₂S
• 分子量: 425.635
• InChiKey: IFFHXWDGBIZSKM-VGSWGCGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S)-5-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-3-[(1R)-1-phenylethyl]-1,3-thiazolidin-4-one 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以75%的产率得到(S)-5-[(3,5-di-tert-butyl-4-hydroxyphenyl)methyl]-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis of enantioenriched 4-thiazolidinone (−)-LY213829 by chemoselective benzylamide cleavage in the presence of a C-S bond

  摘要：

  (R)-2-Methylbenzylamine has been used to covalently ''resolve'' thiol acid 7 and assemble 4-thiazolidinone 8a in one step. Selective deprotection of the 2-methylbenzylamide using lithium in ammonia/THF has been achieved in the presence of a readily hydrogenolyzed C-S bond. Enantioenriched (-)-LY213829 (1) of 98% ee has been prepared by this five step route in 25% yield from aldehyde 2. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00321-7
• 作为产物：
  描述：

  3,5-二叔丁基-4-羟基苯甲醛 在 sodium hydroxide 、 二氢吡啶 、 sodium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 32.5h， 生成 (5S)-5-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-3-[(1R)-1-phenylethyl]-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis of enantioenriched 4-thiazolidinone (−)-LY213829 by chemoselective benzylamide cleavage in the presence of a C-S bond

  摘要：

  (R)-2-Methylbenzylamine has been used to covalently ''resolve'' thiol acid 7 and assemble 4-thiazolidinone 8a in one step. Selective deprotection of the 2-methylbenzylamide using lithium in ammonia/THF has been achieved in the presence of a readily hydrogenolyzed C-S bond. Enantioenriched (-)-LY213829 (1) of 98% ee has been prepared by this five step route in 25% yield from aldehyde 2. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00321-7

文献信息

• Synthesis of enantioenriched 4-thiazolidinone (−)-LY213829 by chemoselective benzylamide cleavage in the presence of a C-S bond
  作者：Marvin M. Hansen、Allen R. Harkness、Vien V. Khau、Michael J. Martinelli、Jack B. Deeter

  DOI：10.1016/0957-4166(96)00321-7

  日期：1996.9

  (R)-2-Methylbenzylamine has been used to covalently ''resolve'' thiol acid 7 and assemble 4-thiazolidinone 8a in one step. Selective deprotection of the 2-methylbenzylamide using lithium in ammonia/THF has been achieved in the presence of a readily hydrogenolyzed C-S bond. Enantioenriched (-)-LY213829 (1) of 98% ee has been prepared by this five step route in 25% yield from aldehyde 2. Copyright (C) 1996 Elsevier Science Ltd