(1S,5R,6R,7R)-6-[(3R)-3-hydroxy-5-phenyl-1-pentenyl]-7-[(4-benzoyl)oxy]-2-oxabicyclo[3.3.0]octan-3-one | 55516-35-3

• 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: (1S,5R,6R,7R)-6-[(3R)-3-hydroxy-5-phenyl-1-pentenyl]-7-[(4-benzoyl)oxy]-2-oxabicyclo[3.3.0]octan-3-one
• 英文别名: benzoic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-hydroxy-5-phenyl-pent-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester；(3aR,4R,5R,6aS)-4-[3R-hydroxy-5-phenyl-1E-pentenyl]-5-(benzoyloxy)-hexahydro-2H-cyclopenta[b]furan-2-one；[(3aR,4R,5R,6aS)-4-[(E,3R)-3-hydroxy-5-phenylpent-1-enyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] benzoate
• CAS: 55516-35-3
• 化学式: C₂₅H₂₆O₅
• 分子量: 406.478
• InChiKey: GWKXXTFDNXEANF-CNVFNLSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1S,5R,6R,7R)-6-[3-acetoxy-5-phenyl-1-pentenyl]-7-[(4-benzoyl)oxy]-2-oxabicyclo[3.3.0]octan-3-one 在 lipase 乙醇 作用下， 以 甲基叔丁基醚 为溶剂， 反应 124.0h， 生成 (1S,5R,6R,7R)-6-[(3R)-3-hydroxy-5-phenyl-1-pentenyl]-7-[(4-benzoyl)oxy]-2-oxabicyclo[3.3.0]octan-3-one
  参考文献：
  名称：

  Enzymatic transformation of a prostaglandin (bimatoprost) intermediate

  摘要：

  提供一种选择性酶促乙酰化贝马前列素中间体的方法。

  公开号：

  US20060247453A1

文献信息

• Improved Process for the Production of Prostaglandins and Prostaglandin Analogs
  申请人：SANDOZ AG

  公开号：EP2143712A1

  公开（公告）日：2010-01-13

  The present invention relates to an improved process for the production of prostaglandins and prostaglandin analogs. In particular, this invention relates to the production of prostaglandins of the PGF2α-series, including latanoprost, travoprost, and bimatoprost, which are active pharmaceutical ingredients used for the reduction of elevated intraocular pressure in patients with glaucoma and ocular hypertension.

  本发明涉及一种改进的用于生产前列腺素和前列腺素类似物的过程。具体而言，本发明涉及PGF2α系列前列腺素的生产，包括拉坦前列醇、曲普前列醇和比马前列醇，这些是用于降低青光眼和眼内高压患者眼内压的活性药用成分。
• [EN] PREPARATION OF PROSTAGLANDIN DERIVATIVES<br/>[FR] PRÉPARATION DE DÉRIVÉS DE PROSTAGLANDINES
  申请人：APTUIT LAURUS PRIVATE LTD

  公开号：WO2012011128A1

  公开（公告）日：2012-01-26

  A process for preparing the prostaglandin derivatives is provided, wherein the benzoyl and p-nitrobenzoyl groups are used as the hydroxyl protective groups. A pharmaceutical composition comprising the prostaglandin derivatives is also provided.

  提供了一种制备前列腺素衍生物的过程，其中苯甲酰和对硝基苯甲酰基被用作羟基保护基团。同时还提供了一种包含前列腺素衍生物的药物组合物。
• Diastereoselective Reduction of the Enone Intermediate of Travoprost
  作者：C. Aswathanarayanappa、E. Bheemappa、Yadav D. Bodke

  DOI：10.1021/op200154p

  日期：2011.9.16

  A scalable process for the diastereoselective reduction of the prochiral enone intermediate 1 has been developed with DEANB/(R)-methyl CBS as reducing agent, to obtain the key intermediate alcohol 15R-isomer 2, used in a process for the manufacture of Travoprost (3). Various advantages of this process against the DMSB reduction assisted by (R)-methyl CBS have been studied. Specific comparison has been made to highlight the salient features of the chosen process on yield and optical purity with those of the DMSB reduction.
• US4346228A
  申请人：——

  公开号：US4346228A

  公开（公告）日：1982-08-24