(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12-(benzoyloxy)-9,11-dihydroxy-4a,8,13,13-tetramethyl-4-(((methylthio)carbonothioyl)oxy)-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate | 150930-82-8

• 英文名称: (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12-(benzoyloxy)-9,11-dihydroxy-4a,8,13,13-tetramethyl-4-(((methylthio)carbonothioyl)oxy)-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate
• CAS: 150930-82-8
• 化学式: C₃₃H₄₀O₁₁S₂
• 分子量: 676.806
• InChiKey: CAFPHSXMFRLYBN-WBFAQAOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  46.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  154.89
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12-(benzoyloxy)-9,11-dihydroxy-4a,8,13,13-tetramethyl-4-(((methylthio)carbonothioyl)oxy)-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以85%的产率得到7,10-dideoxy baccatin
  参考文献：
  名称：

  轻松合成7,10-二脱氧紫杉醇和7-epi-10-脱氧紫杉醇

  摘要：

  由浆果赤霉素III通过Barton脱氧反应，在4个步骤中制备7，10-二脱氧紫杉醇2。类似地，以高收率从7-表紫杉醇一步制备7-表-10-脱氧紫杉醇3。关键反应是氢化三丁基林介导的乙酸C 10的直接还原。

  DOI：

  10.1016/s0040-4039(00)91810-0
• 作为产物：
  描述：

  巴卡丁 III 在 咪唑 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 生成 (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12-(benzoyloxy)-9,11-dihydroxy-4a,8,13,13-tetramethyl-4-(((methylthio)carbonothioyl)oxy)-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate
  参考文献：
  名称：

  Synthesis of 7-deoxy- and 7,10-dideoxytaxol via radical intermediates

  摘要：

  7-Deoxytaxol and 7,10-dideoxytaxol were prepared from baccatin III, employing the Barton deoxygenation procedure and the Holton acylation method at C-13.

  DOI：

  10.1021/jo00071a002

文献信息

• C2 substituted phenyl taxane derivatives and pharmaceutical compositions containing them
  申请人：Florida State University

  公开号：US06339164B1

  公开（公告）日：2002-01-15

  Taxane derivatives having alternative C2 substituents.

  具有替代C2取代基的紫杉烷衍生物。
• C13 amido substituted taxane derivatives and pharmaceutical compositions containing them
  申请人：Florida State University

  公开号：US06369244B1

  公开（公告）日：2002-04-09

  Taxane derivatives having an amino substituted C13 side chain.

  具有氨基取代的C13侧链的紫杉烷衍生物。
• Taxanes having an alkyl substituted side-chain and pharmaceutical compositions containing them
  申请人：Florida State University

  公开号：US06335362B1

  公开（公告）日：2002-01-01

  Taxane derivatives having an alkyl substituted C13 side chain.

  具有烷基取代的C13侧链的紫杉烷衍生物。
• Studies on the photochemistry of taxol®
  作者：Shi-Hui Chen、Vittorio Farina、Stella Huang、Qi Gao、Jerzy Golik、Terrence W. Doyle

  DOI：10.1016/s0040-4020(01)85337-0

  日期：1994.1

  Irradiation of taxol at 280 nm in a Rayonet reactor yielded a novel pentacyclic derivative containing a new bond between C-3 and C-II. The proposed mechanism involves a triplet intermediate and the first event of the oxa-di-pi-merhane rearrangement. Taxane derivatives that lack both the benzoate at C-2 and the benzamide function at C-3' do not undergo the rearrangement, suggesting the intervention of an intramolecular energy transfer. Irradiation at 300 nm also effects extrusion of the C-9 carbonyl, yielding a ring-contracted product.