(5S,7S,8S)-7-((tert-butyldimethylsilyl)oxy)-2,2,3,3,8,11,11,12,12-nonamethyl-5-((R,E)-3-methyl-6-(trimethylsilyl)hex-3-en-5-yn-2-yl)-4,10-dioxa-3,11-disilatridecane | 1428738-04-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (5S,7S,8S)-7-((tert-butyldimethylsilyl)oxy)-2,2,3,3,8,11,11,12,12-nonamethyl-5-((R,E)-3-methyl-6-(trimethylsilyl)hex-3-en-5-yn-2-yl)-4,10-dioxa-3,11-disilatridecane
• CAS: 1428738-04-8
• 化学式: C₃₄H₇₂O₃Si₄
• 分子量: 641.286
• InChiKey: RHUVJCZSFWEVDH-CMSBFFLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.28
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5S,7S,8S)-7-((tert-butyldimethylsilyl)oxy)-2,2,3,3,8,11,11,12,12-nonamethyl-5-((R,E)-3-methyl-6-(trimethylsilyl)hex-3-en-5-yn-2-yl)-4,10-dioxa-3,11-disilatridecane 在 四(三苯基膦)钯 、 叔丁基锂 、 碳酸氢钠 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (1S,6R,7S,9S,10S,E)-7,9,11-tris(tert-butyldimethylsilyloxy)-1-{(2R,4R,5S)-5-[2-(tertbutyldiphenylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-1-(4-methoxybenzyloxy)-5,6,10-trimethyl-3-methyleneundec-4-en-2-one
  参考文献：
  名称：

  Synthesis of the C-1–C-17 Fragment of Amphidinolides C, C2, C3, and F

  摘要：

  The C-1-C-17 fragment of amphidinolides C, C2, C3, and F has been constructed from a trans-2,5-disubstituted dihydrofuranone prepared by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The dihydrofuranone was converted into an aldehyde corresponding to the C-1-C-8 framework, and this was coupled to the C-9-C-17 unit by nucleophilic addition of a vinylic anion.

  DOI：

  10.1021/ol4004838
• 作为产物：
  描述：

  (2R,3R,4S,6S,7S)-4,6,8-tris(tert-butyldimethylsilyloxy)-3,7-dimethyloctan-2-ol 在 sodium hexamethyldisilazane 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (5S,7S,8S)-7-((tert-butyldimethylsilyl)oxy)-2,2,3,3,8,11,11,12,12-nonamethyl-5-((R,E)-3-methyl-6-(trimethylsilyl)hex-3-en-5-yn-2-yl)-4,10-dioxa-3,11-disilatridecane
  参考文献：
  名称：

  Synthesis of the C-1–C-17 Fragment of Amphidinolides C, C2, C3, and F

  摘要：

  The C-1-C-17 fragment of amphidinolides C, C2, C3, and F has been constructed from a trans-2,5-disubstituted dihydrofuranone prepared by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The dihydrofuranone was converted into an aldehyde corresponding to the C-1-C-8 framework, and this was coupled to the C-9-C-17 unit by nucleophilic addition of a vinylic anion.

  DOI：

  10.1021/ol4004838