tert-Butyl [(1R,3S)-1-(hydroxymethyl)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl] carbamate | 1322548-00-4

• 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: tert-Butyl [(1R,3S)-1-(hydroxymethyl)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl] carbamate
• CAS: 1322548-00-4
• 化学式: C₂₂H₃₀N₂O₅S
• 分子量: 434.557
• InChiKey: HZHULGZTZRYUAO-HTAPYJJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.63
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl [(1R,3S)-1-(hydroxymethyl)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl] carbamate 在 三氟化硼乙醚 、 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 48.75h， 生成 C₁₈H₂₈N₂O₃
  参考文献：
  名称：

  Synthesis of (3S)-(tert-butyldimethylsilyloxy)methylcyclopentan-1-one as a key intermediate of sphingosine 1-phosphate-1 receptor agonists

  摘要：

  Herein we report the asymmetric synthesis of (3S)-(tert-butyldimethylsilyloxy)methylcyclopentan-1-one (S)-3 as a practical chiral synthon for a wide range of pharmaceutical and/or natural products, using Lipshutz's asymmetric copper-catalyzed conjugate reduction. This method makes it feasible to prepare a conformationally constrained cyclopentane analogue 12, which is one of the key intermediates for the synthesis of novel sphingosine 1-phosphate-1 receptor agonists. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.015
• 作为产物：
  描述：

  tert-butyl (5R,7S)-7-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}-2-oxo-3-oxa-1-azaspiro[4.4] nonane-1-carboxylate 在 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 tert-Butyl [(1R,3S)-1-(hydroxymethyl)-3-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}cyclopentyl] carbamate
  参考文献：
  名称：

  Synthesis of (3S)-(tert-butyldimethylsilyloxy)methylcyclopentan-1-one as a key intermediate of sphingosine 1-phosphate-1 receptor agonists

  摘要：

  Herein we report the asymmetric synthesis of (3S)-(tert-butyldimethylsilyloxy)methylcyclopentan-1-one (S)-3 as a practical chiral synthon for a wide range of pharmaceutical and/or natural products, using Lipshutz's asymmetric copper-catalyzed conjugate reduction. This method makes it feasible to prepare a conformationally constrained cyclopentane analogue 12, which is one of the key intermediates for the synthesis of novel sphingosine 1-phosphate-1 receptor agonists. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.015