[(1Z,3aR,4S,4aR,8R,8aS,8bR)-8b-hydroxy-8-(hydroxymethyl)-2,2,4a-trimethyl-1-[2-(2-methyl-1,3-dioxolan-2-yl)ethylidene]-7-oxo-3a,4,8,8a-tetrahydro-3H-cyclopenta[a]inden-4-yl] acetate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1Z,3aR,4S,4aR,8R,8aS,8bR)-8b-hydroxy-8-(hydroxymethyl)-2,2,4a-trimethyl-1-[2-(2-methyl-1,3-dioxolan-2-yl)ethylidene]-7-oxo-3a,4,8,8a-tetrahydro-3H-cyclopenta[a]inden-4-yl] acetate
• 化学式: C₂₄H₃₄O₇
• 分子量: 434.53
• InChiKey: KVYUSZDLXCBRTO-FTJGWPQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1Z,3aR,4S,4aR,8R,8aS,8bR)-8b-hydroxy-8-(hydroxymethyl)-2,2,4a-trimethyl-1-[2-(2-methyl-1,3-dioxolan-2-yl)ethylidene]-7-oxo-3a,4,8,8a-tetrahydro-3H-cyclopenta[a]inden-4-yl] acetate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 9.84h， 生成 Acetic acid (3aR,3bS,4R,5S,7aR,8S,8aR)-3a,5-dihydroxy-4-hydroxymethyl-2,2,7a-trimethyl-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-eth-(Z)-ylidene]-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester
  参考文献：
  名称：

  Studies towards the total synthesis of taxoids: a rapid entry into bicyclo[6.4.0]dodecane ring system. Part 1

  摘要：

  We report a short and stereocontrolled synthesis of the taxoid BC-subunit (+)-5 embodying the whole carbon framework and most of the required oxygen functionalities for further elaboration. Enantiomeric purity was secured at an early stage by resolution involving derivatization with (S)-2-acetoxypropionyl chloride on (+/-)-10b. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00434-0
• 作为产物：
  描述：

  在 samarium diiodide 、 四丁基氟化铵 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 50.67h， 生成 [(1Z,3aR,4S,4aR,8R,8aS,8bR)-8b-hydroxy-8-(hydroxymethyl)-2,2,4a-trimethyl-1-[2-(2-methyl-1,3-dioxolan-2-yl)ethylidene]-7-oxo-3a,4,8,8a-tetrahydro-3H-cyclopenta[a]inden-4-yl] acetate
  参考文献：
  名称：

  Arseniyadis, Simeon; Alves, Rosemeire Brondi; De Freitas, Rossimiriam Pereira, Heterocycles, 1997, vol. 46, # 1, p. 727 - 764

  摘要：

  DOI：

文献信息

• Studies towards the total synthesis of taxoids: An efficient formal total synthesis of an A-seco taxane framework
  作者：S. Arseniyadis、Q. Wang、D.V. Yashunsky、T. Kaoudi、R. Brondi Alves、P. Potier

  DOI：10.1016/0040-4039(95)00041-a

  日期：1995.3

  Compounds 6 and 19 embodying the whole carbon framework and suitable functionalities of the taxane skeleton have been assembled starting from readily available chemicals.
• Studies towards the total synthesis of taxoids The aldol-annelation-fragmentation strategy
  作者：S. Arseniyadis、M. Rico Ferreira、J. Quilez del Moral、D.V. Yashunsky、P. Potier

  DOI：10.1016/s0040-4039(97)10703-1

  日期：1998.2

  We describe an aldol-annelation-fragmentation strategy culminating in the stereoselective synthesis of the whole 20-carbon A-seco taxane framework 1 in only 12 linear steps starting from the two achiral aldol partners 2 and 3. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Stereoselective synthesis of an A-seco-taxoid subunit using the Aldol-annelation-fragmentation strategy
  作者：Siméon Arseniyadis、María del Rosario Rico Ferreira、José Quílez del Moral、José Ignacio Martín Hernando、Pierre Potier、Loïc Toupet

  DOI：10.1016/s0040-4039(98)01560-3

  日期：1998.10

  We present a concise route to an optically pure A-seco taxoid framework containing suitable oxygen functionalities for further elaboration. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.