(2R,4R)-2-methyl-4-(trimethylsilyloxy)pentan-1-ol | 681830-33-1

• 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: (2R,4R)-2-methyl-4-(trimethylsilyloxy)pentan-1-ol
• CAS: 681830-33-1
• 化学式: C₁₂H₂₈O₂Si
• 分子量: 232.439
• InChiKey: FCHJZZCGHHMSCI-VXGBXAGGSA-N

物化性质

• 沸点：
  268.1±23.0 °C(Predicted)
• 密度：
  0.870±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  15.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2R,4R)-2-methyl-4-(trimethylsilyloxy)pentan-1-ol 在 四丙基高钌酸铵 N-甲基吲哚酮 、 三氟甲磺酸二丁硼 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.17h， 生成 (4R)-4-benzyl-3-[(2R,3S,4R,6R)-3-hydroxy-4-methyl-2-phenylmethoxy-6-triethylsilyloxyheptanoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Unified Synthesis of C₁₉−C₂₆ Subunits of Amphidinolides B₁, B₂, and B₃ by Exploiting Unexpected Stereochemical Differences in Crimmins' and Evans' Aldol Reactions

  摘要：

  The efficient synthesis of the C-19-C-26 subunit of amphidinolide B-1 and B-2 has been completed using a boron-mediated aldol reaction. The synthesis of the C-19-C-26 subunit of amphidinolide B-3 has also been accomplished through an unexpected anti aldol reaction using a titanium-mediated process. In addition, the first reported examples of a stereochemical discrepancy between the Evans' boron-mediated oxazolidinone and the Crimmins' titanium-mediated oxazolidinethione aldol reactions are disclosed. A working hypothesis is put forth to explain the results.

  DOI：

  10.1021/jo035829l
• 作为产物：
  描述：

  三乙基氯硅烷 在 4-二甲氨基吡啶 、 正丁基锂 、 硼烷铵络合物 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (2R,4R)-2-methyl-4-(trimethylsilyloxy)pentan-1-ol
  参考文献：
  名称：

  Unified Synthesis of C₁₉−C₂₆ Subunits of Amphidinolides B₁, B₂, and B₃ by Exploiting Unexpected Stereochemical Differences in Crimmins' and Evans' Aldol Reactions

  摘要：

  The efficient synthesis of the C-19-C-26 subunit of amphidinolide B-1 and B-2 has been completed using a boron-mediated aldol reaction. The synthesis of the C-19-C-26 subunit of amphidinolide B-3 has also been accomplished through an unexpected anti aldol reaction using a titanium-mediated process. In addition, the first reported examples of a stereochemical discrepancy between the Evans' boron-mediated oxazolidinone and the Crimmins' titanium-mediated oxazolidinethione aldol reactions are disclosed. A working hypothesis is put forth to explain the results.

  DOI：

  10.1021/jo035829l

文献信息

• Total Syntheses of Amphidinolides B1, B4, G1, H1 and Structure Revision of Amphidinolide H2
  作者：Alois Fürstner、Laure C. Bouchez、Louis Morency、Jaques-Alexis Funel、Vilnis Liepins、François-Hugues Porée、Ryan Gilmour、Daniel Laurich、Florent Beaufils、Minoru Tamiya

  DOI：10.1002/chem.200802067

  日期：2009.4.14

  unselective “chemist” when it comes to making the highly cytotoxic amphidinolide macrolides of the B/G/H series. To date, 16 different such compounds have been isolated, all of which could now be approached by a highly convergent and largely catalysis‐based route (see figure). This notion is exemplified by the total synthesis of five prototype members of this family.

  在生产具有高细胞毒性的B / G / H系列安非他命类大环内酯类药物时，自然界是一个非选择性的“化学家”。迄今为止，已分离出16种不同的此类化合物，现在可以通过高度聚合且主要基于催化作用的途径来接近所有这些化合物（见图）。该族的五个原型成员的总合成就是这一概念的例证。