methyl (RS)-5-tris(phenylthio)methylcyclopent-1-enecarboxylate | 1046427-59-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl (RS)-5-tris(phenylthio)methylcyclopent-1-enecarboxylate
• 英文别名: Methyl 5-[tris(phenylsulfanyl)methyl]cyclopentene-1-carboxylate；methyl 5-[tris(phenylsulfanyl)methyl]cyclopentene-1-carboxylate
• CAS: 1046427-59-1
• 化学式: C₂₆H₂₄O₂S₃
• 分子量: 464.673
• InChiKey: VDSVJAALCWAVCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (RS)-5-tris(phenylthio)methylcyclopent-1-enecarboxylate 、 N-苄基异丙胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以92%的产率得到methyl (1RS,2SR,5SR)-2-(N-benzyl-N-isopropylamino)-5-tris(phenylthio)methylcyclopentanecarboxylate
  参考文献：
  名称：

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin

  摘要：

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate with a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide provides an efficient entry to the corresponding homochiral methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tris(phenylthio)methyl-cyclopentane-carboxylate derivatives in >98% de, with subsequent, sequential desulfurisation with Raney Nickel, N-debenzylation and ester hydrolysis furnishing (I R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin in high yield, >98% de and >98% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.016
• 作为产物：
  描述：

  三(苯硫基)甲烷 、 methyl 5-acetoxy-cyclopentene-1-carboxylate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.5h， 以89%的产率得到methyl (RS)-5-tris(phenylthio)methylcyclopent-1-enecarboxylate
  参考文献：
  名称：

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin

  摘要：

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate with a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide provides an efficient entry to the corresponding homochiral methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tris(phenylthio)methyl-cyclopentane-carboxylate derivatives in >98% de, with subsequent, sequential desulfurisation with Raney Nickel, N-debenzylation and ester hydrolysis furnishing (I R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin in high yield, >98% de and >98% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.016

文献信息

• Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin
  作者：Elin Abraham、Stephen G. Davies、Alexander J. Docherty、Kenneth B. Ling、Paul M. Roberts、Angela J. Russell、James E. Thomson、Steven M. Toms

  DOI：10.1016/j.tetasy.2008.05.016

  日期：2008.6

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate with a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide provides an efficient entry to the corresponding homochiral methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tris(phenylthio)methyl-cyclopentane-carboxylate derivatives in >98% de, with subsequent, sequential desulfurisation with Raney Nickel, N-debenzylation and ester hydrolysis furnishing (I R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin in high yield, >98% de and >98% ee. (C) 2008 Elsevier Ltd. All rights reserved.