(4aS,6aR,7S,7aR,10aR,10bS,10cR)-3,3,6a,9,9-Pentamethyl-10-[2-(2-methyl-[1,3]dioxolan-2-yl)-eth-(Z)-ylidene]-6a,7,7a,8,9,10,10b,10c-octahydro-1H,4aH-2,4-dioxa-pentaleno[1,2-a]naphthalene-7,10a-diol | 220487-51-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,6aR,7S,7aR,10aR,10bS,10cR)-3,3,6a,9,9-Pentamethyl-10-[2-(2-methyl-[1,3]dioxolan-2-yl)-eth-(Z)-ylidene]-6a,7,7a,8,9,10,10b,10c-octahydro-1H,4aH-2,4-dioxa-pentaleno[1,2-a]naphthalene-7,10a-diol
• 英文别名: (1S,2R,7S,10R,11S,12R,15Z,16R)-5,5,10,14,14-pentamethyl-15-[2-(2-methyl-1,3-dioxolan-2-yl)ethylidene]-4,6-dioxatetracyclo[8.6.0.02,7.012,16]hexadec-8-ene-11,16-diol
• CAS: 220487-51-4
• 化学式: C₂₅H₃₈O₆
• 分子量: 434.573
• InChiKey: PTCINYGCCVGFFV-MOOKSQOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4aS,6aR,7S,7aR,10aR,10bS,10cR)-3,3,6a,9,9-Pentamethyl-10-[2-(2-methyl-[1,3]dioxolan-2-yl)-eth-(Z)-ylidene]-6a,7,7a,8,9,10,10b,10c-octahydro-1H,4aH-2,4-dioxa-pentaleno[1,2-a]naphthalene-7,10a-diol 在 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 bis(acetylacetonate)oxovanadium 作用下， 以 乙醚 、 癸烷 、 苯 为溶剂， 反应 0.42h， 生成 (1R,2S,3'R,4R,5R,10R,11S,12R,13R,16R,17S)-1,7,7,14,14-pentamethyl-3'-[(2-methyl-1,3-dioxolan-2-yl)methyl]spiro[3,6,8-trioxapentacyclo[9.6.0.02,4.05,10.012,16]heptadecane-13,2'-oxirane]-12,17-diol
  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：

  [(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 hydroxide 、 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 11.75h， 生成 (4aS,6aR,7S,7aR,10aR,10bS,10cR)-3,3,6a,9,9-Pentamethyl-10-[2-(2-methyl-[1,3]dioxolan-2-yl)-eth-(Z)-ylidene]-6a,7,7a,8,9,10,10b,10c-octahydro-1H,4aH-2,4-dioxa-pentaleno[1,2-a]naphthalene-7,10a-diol
  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