(1S,2S,3'R,4R,5R,10R,11S,12R,13R,16S)-12-hydroxy-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]-17-one | 220487-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3'R,4R,5R,10R,11S,12R,13R,16S)-12-hydroxy-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]-17-one
• CAS: 220487-53-6
• 化学式: C₂₅H₃₆O₈
• 分子量: 464.556
• InChiKey: MDKCLHGBJSIIFK-DNTRRNRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,2S,3'R,4R,5R,10R,11S,12R,13R,16S)-12-hydroxy-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]-17-one 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.17h， 生成 [(1S,2S,3'R,4R,5R,10R,11S,12R,13R,16R,17S)-12-hydroxy-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]-17-yl] methanesulfonate
  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 叔丁基过氧化氢 、 sodium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 bis(acetylacetonate)oxovanadium 、 potassium carbonate 、 对甲苯磺酸 、 2,2-二甲氧基丙烷 作用下， 以 甲醇 、 癸烷 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 12.0h， 生成 (1S,2S,3'R,4R,5R,10R,11S,12R,13R,16S)-12-hydroxy-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]-17-one
  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

文献信息

• 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.