(3R,4S,5R,6S)-2,4-Dimethyl-5-<(2-methoxyethoxy)methoxy>-6-(p-methoxyphenyl)-1-hepten-3-ol | 147879-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3R,4S,5R,6S)-2,4-Dimethyl-5-<(2-methoxyethoxy)methoxy>-6-(p-methoxyphenyl)-1-hepten-3-ol
• 英文别名: (3R,4R,5R,6S)-5-(2-methoxyethoxymethoxy)-6-(4-methoxyphenyl)-2,4-dimethylhept-1-en-3-ol
• CAS: 147879-12-7
• 化学式: C₂₀H₃₂O₅
• 分子量: 352.471
• InChiKey: BHPMKDZBSZNLGY-ACZWYYKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R,6S)-2,4-Dimethyl-5-<(2-methoxyethoxy)methoxy>-6-(p-methoxyphenyl)-1-hepten-3-ol 在 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 bis(acetylacetonate)oxovanadium 、 三氟化硼乙醚 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 41.25h， 生成 (2R,3R,4S,5R,6S)-1-Acetoxy-2,3-(carbonyldioxy)-2,4-dimethyl-5-<(2-methoxyethoxy)methoxy>-6-(p-methoxyphenyl)-1-heptanol
  参考文献：
  名称：

  Efficient and highly stereoselective syntheses of enantiomerically enriched C(1)-C(7) subunits of erythronolides

  摘要：

  Stereocontrolled efficient syntheses of the C(1)-C(7) fragments of deoxyerythronolide and erythronolide seco acids are described. The key step of these syntheses involves a highly stereoselective aldol condensation between an enantiomerically enriched 2-arylpropanal and the lithium enolate of the racemic 2-methyl-5-norbornenyl ethyl ketone, which establishes in one operation the relative and absolute configurations of the three stereocenters C(2), C(3), and C(4). After syn-selective reductions of the carbonyl group, the configuration required at carbon C(6) was introduced by highly selective reactions carried out on the double bond regenerated by a thermal cycloreversion.

  DOI：

  10.1021/jo00063a009
• 作为产物：
  描述：

  (S)-2-(4-methoxyphenyl)propan-1-ol 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 N,N-二异丙基乙胺 、 六甲基二硅氮烷 、 lithium iodide 作用下， 以 二氯甲烷 为溶剂， -90.0~500.0 ℃ 、1.33 Pa 条件下， 反应 34.58h， 生成 (3R,4S,5R,6S)-2,4-Dimethyl-5-<(2-methoxyethoxy)methoxy>-6-(p-methoxyphenyl)-1-hepten-3-ol
  参考文献：
  名称：

  Efficient and highly stereoselective syntheses of enantiomerically enriched C(1)-C(7) subunits of erythronolides

  摘要：

  Stereocontrolled efficient syntheses of the C(1)-C(7) fragments of deoxyerythronolide and erythronolide seco acids are described. The key step of these syntheses involves a highly stereoselective aldol condensation between an enantiomerically enriched 2-arylpropanal and the lithium enolate of the racemic 2-methyl-5-norbornenyl ethyl ketone, which establishes in one operation the relative and absolute configurations of the three stereocenters C(2), C(3), and C(4). After syn-selective reductions of the carbonyl group, the configuration required at carbon C(6) was introduced by highly selective reactions carried out on the double bond regenerated by a thermal cycloreversion.

  DOI：

  10.1021/jo00063a009

文献信息

• Efficient and highly stereoselective syntheses of enantiomerically enriched C(1)-C(7) subunits of erythronolides
  作者：Mohammed Ahmar、Isabelle Romain、Robert Bloch

  DOI：10.1021/jo00063a009

  日期：1993.5

  Stereocontrolled efficient syntheses of the C(1)-C(7) fragments of deoxyerythronolide and erythronolide seco acids are described. The key step of these syntheses involves a highly stereoselective aldol condensation between an enantiomerically enriched 2-arylpropanal and the lithium enolate of the racemic 2-methyl-5-norbornenyl ethyl ketone, which establishes in one operation the relative and absolute configurations of the three stereocenters C(2), C(3), and C(4). After syn-selective reductions of the carbonyl group, the configuration required at carbon C(6) was introduced by highly selective reactions carried out on the double bond regenerated by a thermal cycloreversion.