Z-2-acetoxy-2-acetyl-5,9-dimethyl-10-hydroxy-deca-4-enoic acid tert-butyl ester | 412042-98-9

• 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: Z-2-acetoxy-2-acetyl-5,9-dimethyl-10-hydroxy-deca-4-enoic acid tert-butyl ester
• 英文别名: tert-butyl (Z)-2-acetyl-2-acetyloxy-10-hydroxy-5,9-dimethyldec-4-enoate
• CAS: 412042-98-9
• 化学式: C₂₀H₃₄O₆
• 分子量: 370.486
• InChiKey: IWHUXMOSYORJGT-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Z-2-acetoxy-2-acetyl-5,9-dimethyl-10-hydroxy-deca-4-enoic acid tert-butyl ester 在 Burkholderia cepacia lipase 、 4-二甲氨基吡啶 、 sodium phosphate buffer 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 (Z)-(S)-11-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-6,10-dimethyl-undec-5-en-2-one
  参考文献：
  名称：

  Synthesis and resolution of a key building block for epothilones: a comparison of asymmetric synthesis, chemical and enzymatic resolution

  摘要：

  The asymmetric synthesis and kinetic resolution of a series of acyloins (alpha-hydroxy ketones) suitable as building blocks for the northern half of epothilones was studied. Three methods were applied to obtain nonracemic compounds at the eventual epothilone C15-position: asymmetric synthesis with Evans' auxiliary, chemical resolution and enzymatic resolution. The success rate in small scale applications increased in the order given, and the enzymatic resolution was studied in more detail. Out of a set of nine lipases and esterases, lipases from Burkholderia cepacia, Pseudomonas sp., lipase B from Candida antarctica and recombinant esterases from Streptomyces diastatochromogenes exhibited the highest enantioselectivities with E-values ranging from 60 to >200. Pig liver esterase exhibited inverse enantiopreference and only with recombinant enzyme could a moderate selectivity (E = 50, commercial PLE: E = 8) be observed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.048
• 作为产物：
  描述：

  (Z)-2-acetoxy-2-acetyl-5,9-dimethyldeca-4,8-dienoic acid tert-butyl ester 在 Ru[(R)-BINAP](OAc)2 叔丁基过氧化氢 、 selenium(IV) oxide 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、10.0 MPa 条件下， 反应 73.0h， 生成 Z-2-acetoxy-2-acetyl-5,9-dimethyl-10-hydroxy-deca-4-enoic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and resolution of a key building block for epothilones: a comparison of asymmetric synthesis, chemical and enzymatic resolution

  摘要：

  The asymmetric synthesis and kinetic resolution of a series of acyloins (alpha-hydroxy ketones) suitable as building blocks for the northern half of epothilones was studied. Three methods were applied to obtain nonracemic compounds at the eventual epothilone C15-position: asymmetric synthesis with Evans' auxiliary, chemical resolution and enzymatic resolution. The success rate in small scale applications increased in the order given, and the enzymatic resolution was studied in more detail. Out of a set of nine lipases and esterases, lipases from Burkholderia cepacia, Pseudomonas sp., lipase B from Candida antarctica and recombinant esterases from Streptomyces diastatochromogenes exhibited the highest enantioselectivities with E-values ranging from 60 to >200. Pig liver esterase exhibited inverse enantiopreference and only with recombinant enzyme could a moderate selectivity (E = 50, commercial PLE: E = 8) be observed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.048

文献信息

• EPOTHILON-SYNTHESEBAUSTEINE I: UNSYMMETRISCH SUBSTITUIERTE ACYLOINE UND ACYLOINDERIVATE, VERFAHREN ZU DEREN HERSTELLUNG SOWIE DEREN VERWENDUNG ZUR HERSTELLUNG VON EPOTHILONEN UND EPOTHILONDERIVATEN
  申请人：R&D-Biopharmaceuticals

  公开号：EP1358144B1

  公开（公告）日：2006-12-27