(5S,6S,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-2,4,13-trioxa-14-silahexadec-8-en-7-one | 1426146-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,6S,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-2,4,13-trioxa-14-silahexadec-8-en-7-one
• 英文别名: (E,1S,2S,6R,7R)-7,8-bis[[tert-butyl(dimethyl)silyl]oxy]-1-[(2R,4R,5S)-5-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-4-methyloxolan-2-yl]-1,2-bis(methoxymethoxy)-5,6-dimethyloct-4-en-3-one
• CAS: 1426146-01-1
• 化学式: C₄₉H₈₄O₉Si₃
• 分子量: 901.457
• InChiKey: XDIWLECJDKFFEX-KVZPUHJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.29
• 重原子数：
  61
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (5S,6S,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-2,4,13-trioxa-14-silahexadec-8-en-7-one 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 1.08h， 生成 (5S,6R,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-7-methylene-2,4,13-trioxa-14-silahexadec-8-ene
  参考文献：
  名称：

  Syntheses of the C1–C14 and C15–C25 Fragments of Amphidinolide C

  摘要：

  Divergent syntheses of the C1-C14 and C15-C25 fragments of amphidinolide C have been achieved. The synthesis of the C15-C25 fragment featured cobalt-catalyzed modified Mukaiyama aerobic alkenol cyclization and sulfur-directed regiocontrolled Wacker oxidation of an internal alkene. The C1-C14 fragment was established by alkenyllithium addition to an aldehyde followed by a challenging olefination of a highly inert C9 ketone.

  DOI：

  10.1021/ol303515h
• 作为产物：
  描述：

  methyl 2-((2S,3R,5R)-5-((5S,6R)-9,9-diethyl-6-(methoxymethoxy)-2,4,8-trioxa-9-silaundecan-5-yl)-3-methyltetrahydrofuran-2-yl)acetate 在 吡啶 、 咪唑 、 lithium aluminium tetrahydride 、 正丁基锂 、 三氧化硫吡啶 、 4-甲基苯磺酸吡啶 、 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 8.75h， 生成 (5S,6S,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-2,4,13-trioxa-14-silahexadec-8-en-7-one
  参考文献：
  名称：

  Syntheses of the C1–C14 and C15–C25 Fragments of Amphidinolide C

  摘要：

  Divergent syntheses of the C1-C14 and C15-C25 fragments of amphidinolide C have been achieved. The synthesis of the C15-C25 fragment featured cobalt-catalyzed modified Mukaiyama aerobic alkenol cyclization and sulfur-directed regiocontrolled Wacker oxidation of an internal alkene. The C1-C14 fragment was established by alkenyllithium addition to an aldehyde followed by a challenging olefination of a highly inert C9 ketone.

  DOI：

  10.1021/ol303515h

文献信息

• Syntheses of the C1–C14 and C15–C25 Fragments of Amphidinolide C
  作者：Dimao Wu、Craig J. Forsyth

  DOI：10.1021/ol303515h

  日期：2013.3.15

  Divergent syntheses of the C1-C14 and C15-C25 fragments of amphidinolide C have been achieved. The synthesis of the C15-C25 fragment featured cobalt-catalyzed modified Mukaiyama aerobic alkenol cyclization and sulfur-directed regiocontrolled Wacker oxidation of an internal alkene. The C1-C14 fragment was established by alkenyllithium addition to an aldehyde followed by a challenging olefination of a highly inert C9 ketone.