methyl (E,2S,6S,8R)-9-[tert-butyl(diphenyl)silyl]oxy-2,4,6,8-tetramethylnon-3-enoate | 273738-37-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (E,2S,6S,8R)-9-[tert-butyl(diphenyl)silyl]oxy-2,4,6,8-tetramethylnon-3-enoate
• CAS: 273738-37-7
• 化学式: C₃₀H₄₄O₃Si
• 分子量: 480.763
• InChiKey: WHWOMTXWYLJYGD-OADBEPRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E,2S,6S,8R)-9-[tert-butyl(diphenyl)silyl]oxy-2,4,6,8-tetramethylnon-3-enoate 在 4-二甲氨基吡啶 、 copper(l) iodide 、 二异丁基氢化铝 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (E)-(2R,4S,8R)-2,4,6,8-tetramethyl-6-decen-1-ol
  参考文献：
  名称：

  Synthesis (and Alternative Proof of Configuration) of the Scyphostatin C(1‘)−C(20‘) Trienoyl Fragment

  摘要：

  [GRAPHICS]Each of four diastereomers of structure 2, corresponding to the lipophilic side chain of scyphostatin (1), were prepared. Careful analysis of their NMR spectral data and comparison with those of the natural product corroborates the recently reported (Org. Lett. 2000, 2, 505) stereochemical assignment. A strategy for the stereoselective synthesis of 2 has been achieved.

  DOI：

  10.1021/ol0058386
• 作为产物：
  描述：

  (2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate 在 4-二甲氨基吡啶 、 正丁基锂 、 二氯二茂锆 、 三甲基铝 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 59.08h， 生成 methyl (E,2S,6S,8R)-9-[tert-butyl(diphenyl)silyl]oxy-2,4,6,8-tetramethylnon-3-enoate
  参考文献：
  名称：

  Synthesis (and Alternative Proof of Configuration) of the Scyphostatin C(1‘)−C(20‘) Trienoyl Fragment

  摘要：

  [GRAPHICS]Each of four diastereomers of structure 2, corresponding to the lipophilic side chain of scyphostatin (1), were prepared. Careful analysis of their NMR spectral data and comparison with those of the natural product corroborates the recently reported (Org. Lett. 2000, 2, 505) stereochemical assignment. A strategy for the stereoselective synthesis of 2 has been achieved.

  DOI：

  10.1021/ol0058386

文献信息

• Synthesis (and Alternative Proof of Configuration) of the Scyphostatin C(1‘)−C(20‘) Trienoyl Fragment
  作者：Thomas R. Hoye、Manomi A. Tennakoon

  DOI：10.1021/ol0058386

  日期：2000.5.1

  [GRAPHICS]Each of four diastereomers of structure 2, corresponding to the lipophilic side chain of scyphostatin (1), were prepared. Careful analysis of their NMR spectral data and comparison with those of the natural product corroborates the recently reported (Org. Lett. 2000, 2, 505) stereochemical assignment. A strategy for the stereoselective synthesis of 2 has been achieved.