(1S,3S,7S,10R,11S,12S,16R)-3-acetyl-7,11-dihydroxy-8,8,10,12-tetramethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione | 219557-15-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (1S,3S,7S,10R,11S,12S,16R)-3-acetyl-7,11-dihydroxy-8,8,10,12-tetramethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• CAS: 219557-15-0
• 化学式: C₂₁H₃₄O₇
• 分子量: 398.497
• InChiKey: LHMVYYQODSLFLX-VCLQVUGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,3S,7S,10R,11S,12S,16R)-3-acetyl-7,11-dihydroxy-8,8,10,12-tetramethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 、 柠檬酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-Methyl-thiazole-4-carboxylic acid 1-((1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadec-3-yl)-ethyl ester
  参考文献：
  名称：

  Oxidative and reductive transformations of epothilone A

  摘要：

  The C7 hydroxy group of cytotoxic epothilone A was selectively oxidized using PDC. A selective oxidation of the C3 hydroxy group was accomplished with Me2S/(PhCO2)(2) after in situ protection of C7-OH. Reduction of epothilone A or of a C5, C7 dioxo derivative with NaBH4 proceeded at the C5 carbonyl group. Oxidation and hydrogenation of the C16-C17 double bond proved to be difficult but it was easily cleaved with ozone and the resulting keto derivative was transformed to epothilone analogs with different side chains. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00545-9
• 作为产物：
  描述：

  西洛他唑 在 二甲基硫 、 臭氧 作用下， 生成 (1S,3S,7S,10R,11S,12S,16R)-3-acetyl-7,11-dihydroxy-8,8,10,12-tetramethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
  参考文献：
  名称：

  Oxidative and reductive transformations of epothilone A

  摘要：

  The C7 hydroxy group of cytotoxic epothilone A was selectively oxidized using PDC. A selective oxidation of the C3 hydroxy group was accomplished with Me2S/(PhCO2)(2) after in situ protection of C7-OH. Reduction of epothilone A or of a C5, C7 dioxo derivative with NaBH4 proceeded at the C5 carbonyl group. Oxidation and hydrogenation of the C16-C17 double bond proved to be difficult but it was easily cleaved with ozone and the resulting keto derivative was transformed to epothilone analogs with different side chains. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00545-9

文献信息

• Epothilon-Derivate, ihre Herstellung und Verwendung
  申请人：Gesellschaft für Biotechnologische Forschung mbH (GBF)

  公开号：EP1186606B2

  公开（公告）日：2011-09-07
• Oxidative and reductive transformations of epothilone A
  作者：Michael Sefkow、Michael Kiffe、Dietmar Schummer、Gerhard Höfle

  DOI：10.1016/s0960-894x(98)00545-9

  日期：1998.11

  The C7 hydroxy group of cytotoxic epothilone A was selectively oxidized using PDC. A selective oxidation of the C3 hydroxy group was accomplished with Me2S/(PhCO2)(2) after in situ protection of C7-OH. Reduction of epothilone A or of a C5, C7 dioxo derivative with NaBH4 proceeded at the C5 carbonyl group. Oxidation and hydrogenation of the C16-C17 double bond proved to be difficult but it was easily cleaved with ozone and the resulting keto derivative was transformed to epothilone analogs with different side chains. (C) 1998 Elsevier Science Ltd. All rights reserved.