Methyl 2(S)-hydroxy-3(R)-(2-carbomethoxyethylthio)-3-[2-(8-phenyloctyl)phenyl] propionate | 120521-75-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 2(S)-hydroxy-3(R)-(2-carbomethoxyethylthio)-3-[2-(8-phenyloctyl)phenyl] propionate
• 英文别名: methyl (2S,3R)-2-hydroxy-3-(3-methoxy-3-oxopropyl)sulfanyl-3-[2-(8-phenyloctyl)phenyl]propanoate
• CAS: 120521-75-7
• 化学式: C₂₈H₃₈O₅S
• 分子量: 486.673
• InChiKey: RLNSCIIYYLRFGZ-KAYWLYCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  34
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2(S)-hydroxy-3(R)-(2-carbomethoxyethylthio)-3-[2-(8-phenyloctyl)phenyl] propionate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 (2S,3R)-3-(2-羧基乙基硫基)-2-羟基-3-[2-(8-苯基辛基)苯基]丙酸
  参考文献：
  名称：

  A practical, enantioselective synthesis of SK&F 104353

  摘要：

  A highly efficient and enantioselective (>99.5% ee) synthesis of the title compound has been accomplished. Key steps include (1) epoxidation of unsaturated ketone 7 in the presence of a polyamino acid to afford compound 8 in >95% ee, (2) regioselective Baeyer-Villiger rearrangement of epoxy ketone 8 to afford glycidic ester 9, and (3) regioselective (35:1) opening of lithium glycidate 13 at C-3 with methyl 3-mercaptopropionate. The approach is economical, and all transformations proceed in high yield and are amenable to large-scale preparation.

  DOI：

  10.1021/jo00075a019
• 作为产物：
  描述：

  重氮甲烷 、 (2S,3R)-3-(2-羧基乙基硫基)-2-羟基-3-[2-(8-苯基辛基)苯基]丙酸 以 乙醚 为溶剂， 生成 Methyl 2(S)-hydroxy-3(R)-(2-carbomethoxyethylthio)-3-[2-(8-phenyloctyl)phenyl] propionate
  参考文献：
  名称：

  Leukotriene antagonists

  摘要：

  公开号：

  EP0296732B1

文献信息

• SHU, ARTHUR Y. L.;HEYS, J. RICHARD;MASTROCOLA, ANTONIETTA R., J. LABELL. COMPOUNDS AND RADIOPHARM., 28,(1990) N, C. 215-234
  作者：SHU, ARTHUR Y. L.、HEYS, J. RICHARD、MASTROCOLA, ANTONIETTA R.

  DOI：——

  日期：——
• US5314918A
  申请人：——

  公开号：US5314918A

  公开（公告）日：1994-05-24
• Leukotriene antagonists
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0296732B1

  公开（公告）日：1991-10-09
• A practical, enantioselective synthesis of SK&F 104353
  作者：Joseph R. Flisak、Kerry J. Gombatz、Monica M. Holmes、Alvydas A. Jarmas、Ivan Lantos、Wilford L. Mendelson、Vance J. Novack、James J. Remich、Lawrence Snyder

  DOI：10.1021/jo00075a019

  日期：1993.11

  A highly efficient and enantioselective (>99.5% ee) synthesis of the title compound has been accomplished. Key steps include (1) epoxidation of unsaturated ketone 7 in the presence of a polyamino acid to afford compound 8 in >95% ee, (2) regioselective Baeyer-Villiger rearrangement of epoxy ketone 8 to afford glycidic ester 9, and (3) regioselective (35:1) opening of lithium glycidate 13 at C-3 with methyl 3-mercaptopropionate. The approach is economical, and all transformations proceed in high yield and are amenable to large-scale preparation.