[(1Z,3aR,4S,4aR,8R,8aS,8bR)-4-acetyloxy-8b-hydroxy-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-8-yl]methyl (2S)-2-acetyloxypropanoate | 214902-84-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(1Z,3aR,4S,4aR,8R,8aS,8bR)-4-acetyloxy-8b-hydroxy-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-8-yl]methyl (2S)-2-acetyloxypropanoate
• CAS: 214902-84-8
• 化学式: C₂₉H₄₀O₁₀
• 分子量: 548.631
• InChiKey: IGTFLAOAFWWDFD-VGFVRSDNSA-N

物化性质

• 沸点：
  624.023±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.265±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(1Z,3aR,4S,4aR,8R,8aS,8bR)-4-acetyloxy-8b-hydroxy-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-8-yl]methyl (2S)-2-acetyloxypropanoate 在 sodium tetrahydroborate 、 cerium(III) chloride 、 potassium carbonate 、 对甲苯磺酸 、 2,2-二甲氧基丙烷 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 9.75h， 生成 Acetic acid (4aS,6aR,7S,7aR,10aR,10bS,10cR)-10a-hydroxy-3,3,6a,9,9-pentamethyl-10-[2-(2-methyl-[1,3]dioxolan-2-yl)-eth-(Z)-ylidene]-4a,6a,7,7a,8,9,10,10a,10b,10c-decahydro-1H-2,4-dioxa-pentaleno[1,2-a]naphthalen-7-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：

  Acetic acid (3aR,3bS,4R,7aR,8S,8aR)-4-hydroxymethyl-2,2,7a-trimethyl-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-eth-(Z)-ylidene]-5-oxo-3a-trimethylsilanyloxy-1,2,3,3a,3b,4,5,7a,8,8a-decahydro-cyclopenta[a]inden-8-yl ester 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [(1Z,3aR,4S,4aR,8R,8aS,8bR)-4-acetyloxy-8b-hydroxy-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-8-yl]methyl (2S)-2-acetyloxypropanoate
  参考文献：
  名称：

  Studies towards the total synthesis of taxoids The aldol-annelation-fragmentation strategy

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(97)10703-1