(3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one | 213390-88-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one
• 英文别名: (1R,3E,5E,9S,10R,11S,13E,15R,17R,19E,21S,24R,25R,27S,29R)-11-hydroxy-15,21-dimethoxy-27-(4-methoxyphenyl)-10,17,20,24,29-pentamethyl-9-[(2S)-1-tri(propan-2-yl)silyloxypropan-2-yl]-8,26,28-trioxabicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one
• CAS: 213390-88-6
• 化学式: C₅₂H₈₆O₉Si
• 分子量: 883.335
• InChiKey: XQMSZGNVVMFCNN-NOZKDPJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.12
• 重原子数：
  62
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one 在 titanium(IV) isopropylate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到(3E,5E,11E,17E)-(1R,9S,13R,15R,19S,22R,23R,25S,27R)-9-((1S,2S,3S)-2-Hydroxy-1,3-dimethyl-4-triisopropylsilanyloxy-butyl)-13,19-dimethoxy-25-(4-methoxy-phenyl)-15,18,22,27-tetramethyl-8,24,26-trioxa-bicyclo[21.3.1]heptacosa-3,5,11,17-tetraen-7-one
  参考文献：
  名称：

  Studies in marine macrolide synthesis: Construction of a 24-membered macrocyclic intermediate for aplyronine A

  摘要：

  The C-1-C-27 macrolide 2, which contains 11 stereocentres and 4 double bonds, was constructed by an efficient 3-component coupling followed by a macrolactonisation/isomerization sequence. Key steps were the alkylation of the dianion of phosphonate 5 with iodide 7 and a Ba(OH)(2)-mediated HWE reaction with 6 to install the trisubstituted double bond. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01192-7
• 作为产物：
  描述：

  tert-Butyl-{(2E,4E)-6-[(2S,4R,5R,6S)-6-((S)-2-iodo-1-methyl-ethyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-hexa-2,4-dienyloxy}-dimethyl-silane 在 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 barium dihydroxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 正丁基锂 、 dimethyl sulfide borane 、 (R)-proline derived oxazaborolidine 、 pH₇ buffer 、 2,4,6-三氯苯甲酰氯 、 sodium hydride 、 氟化氢吡啶 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 氯仿 、 水 、 叔丁醇 为溶剂， 反应 32.5h， 生成 (3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one
  参考文献：
  名称：

  Studies in marine macrolide synthesis: Construction of a 24-membered macrocyclic intermediate for aplyronine A

  摘要：

  The C-1-C-27 macrolide 2, which contains 11 stereocentres and 4 double bonds, was constructed by an efficient 3-component coupling followed by a macrolactonisation/isomerization sequence. Key steps were the alkylation of the dianion of phosphonate 5 with iodide 7 and a Ba(OH)(2)-mediated HWE reaction with 6 to install the trisubstituted double bond. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01192-7

文献信息

• Studies in marine macrolide synthesis: Construction of a 24-membered macrocyclic intermediate for aplyronine A
  作者：Ian Paterson、Michael D Woodrow、Cameron J Cowden

  DOI：10.1016/s0040-4039(98)01192-7

  日期：1998.8

  The C-1-C-27 macrolide 2, which contains 11 stereocentres and 4 double bonds, was constructed by an efficient 3-component coupling followed by a macrolactonisation/isomerization sequence. Key steps were the alkylation of the dianion of phosphonate 5 with iodide 7 and a Ba(OH)(2)-mediated HWE reaction with 6 to install the trisubstituted double bond. (C) 1998 Elsevier Science Ltd. All rights reserved.