(3R,4S,5R,6R)-6-(tert-butyldimethylsiloxy)-2,4-dimethyl-5-methoxy-1-penten-3-ol | 329366-73-6

• 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: (3R,4S,5R,6R)-6-(tert-butyldimethylsiloxy)-2,4-dimethyl-5-methoxy-1-penten-3-ol
• CAS: 329366-73-6
• 化学式: C₁₆H₃₄O₃Si
• 分子量: 302.53
• InChiKey: XHRQFDXUFJULCJ-LJISPDSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R,6R)-6-(tert-butyldimethylsiloxy)-2,4-dimethyl-5-methoxy-1-penten-3-ol 在 吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 23.91h， 生成 (2R,6S,7R,8R,4E)-8-(tert-butyldimethylsiloxy)-7-methoxy-2,4,6-trimethyl-4-nonenoic acid
  参考文献：
  名称：

  A Total Synthesis of Herboxidiene Methyl Ester

  摘要：

  The total synthesis of the methyl ester, 35, of herboxidiene (1, a.k.a. GEX1A and TAN-1609), a polyketide displaying both herbicidal and anti-tumor activity, is described. The convergent reaction sequence involves, in its closing stages, the union of the phosphine oxide 3 with the aldehyde 21 to deliver, via a Horner-Wittig reaction with accompanying epimerization at C12, compound 33 that after deprotection affords an alcohol, 34, capable of participating in a regio- and diastereo-selective epoxidation reaction to give target 35. Phosphine oxide 3 was prepared via the intramolecular hetero-Michael addition of a secondary alcohol to a tethered and Z-configured acrylate while aldehyde 21 was generated, in the crucial step of the relevant reaction sequence, via an Ireland-Claisen rearrangement reaction.

  DOI：

  10.3987/com-12-12597
• 作为产物：
  描述：

  (2R,3R,4S)-3-methoxy-4-methyl-5-(phenylmethoxy)pentan-2-ol 在 咪唑 、 pyridine-SO3 complex 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 叔丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， -78.0~78.0 ℃ 、101.33 kPa 条件下， 反应 7.75h， 生成 (3R,4S,5R,6R)-6-(tert-butyldimethylsiloxy)-2,4-dimethyl-5-methoxy-1-penten-3-ol
  参考文献：
  名称：

  A Total Synthesis of Herboxidiene Methyl Ester

  摘要：

  The total synthesis of the methyl ester, 35, of herboxidiene (1, a.k.a. GEX1A and TAN-1609), a polyketide displaying both herbicidal and anti-tumor activity, is described. The convergent reaction sequence involves, in its closing stages, the union of the phosphine oxide 3 with the aldehyde 21 to deliver, via a Horner-Wittig reaction with accompanying epimerization at C12, compound 33 that after deprotection affords an alcohol, 34, capable of participating in a regio- and diastereo-selective epoxidation reaction to give target 35. Phosphine oxide 3 was prepared via the intramolecular hetero-Michael addition of a secondary alcohol to a tethered and Z-configured acrylate while aldehyde 21 was generated, in the crucial step of the relevant reaction sequence, via an Ireland-Claisen rearrangement reaction.

  DOI：

  10.3987/com-12-12597