(2R,4S)-4-[(2'R,4'S,5'S)-2'-(4-methoxyphenyl)-5'-methyl-1',3'-dioxan-4-yl]-2-methylpentan-1-ol | 124755-30-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,4S)-4-[(2'R,4'S,5'S)-2'-(4-methoxyphenyl)-5'-methyl-1',3'-dioxan-4-yl]-2-methylpentan-1-ol
• 英文别名: (2R,4S)-4-[(2R,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-2-methylpentan-1-ol
• CAS: 124755-30-2
• 化学式: C₁₈H₂₈O₄
• 分子量: 308.418
• InChiKey: ZWNTYYUQGKHEIF-PUQNWLDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4S)-4-[(2'R,4'S,5'S)-2'-(4-methoxyphenyl)-5'-methyl-1',3'-dioxan-4-yl]-2-methylpentan-1-ol 在 咪唑 、 二异丁基氢化铝 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 25.0h， 生成 (2S,3S,4S,6R)-3-(4-methoxybenzyloxy)-2,4,6,-trimethyl-7-(triisopropylsilyloxy)heptan-1-ol
  参考文献：
  名称：

  Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin

  摘要：

  A short and efficient total synthesis of 10-deoxymethynolide (2c), the aglycon of 10-deoxymethymycin (1c), has been accomplished in 16 steps and 12% overall yield from (S)-3-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (15c). The synthesis features an expeditious preparation of (+)-5a, a synthetic equivalent of the Prelog-Djerassi lactonic acid, and the construction of a 12-membered lactone through an intramolecular Nozaki-Hiyama-Kishi coupling reaction.

  DOI：

  10.1021/jo9809433
• 作为产物：
  描述：

  (2S,3R,4S)-5-benzyloxy-2,3-dimethylpentane-1,4-diol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 camphor-10-sulfonic acid 、 potassium tert-butylate 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 46.5h， 生成 (2R,4S)-4-[(2'R,4'S,5'S)-2'-(4-methoxyphenyl)-5'-methyl-1',3'-dioxan-4-yl]-2-methylpentan-1-ol
  参考文献：
  名称：

  Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin

  摘要：

  A short and efficient total synthesis of 10-deoxymethynolide (2c), the aglycon of 10-deoxymethymycin (1c), has been accomplished in 16 steps and 12% overall yield from (S)-3-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (15c). The synthesis features an expeditious preparation of (+)-5a, a synthetic equivalent of the Prelog-Djerassi lactonic acid, and the construction of a 12-membered lactone through an intramolecular Nozaki-Hiyama-Kishi coupling reaction.

  DOI：

  10.1021/jo9809433

文献信息

• Synthesis of polypropionate subunits by SN2' addition of cuprates to nonracemic acyclic vinyloxiranes
  作者：James A. Marshall、Bruce E. Blough

  DOI：10.1021/jo00292a031

  日期：1990.3
• MARSHALL, JAMES A.;BLOUGH, BRUCE E., J. ORG. CHEM., 55,(1990) N, C. 1540-1547
  作者：MARSHALL, JAMES A.、BLOUGH, BRUCE E.

  DOI：——

  日期：——
• Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin
  作者：Ronaldo A. Pilli、Carlos Kleber Z. de Andrade、Carlos Roberto O. Souto、Armin de Meijere

  DOI：10.1021/jo9809433

  日期：1998.10.1

  A short and efficient total synthesis of 10-deoxymethynolide (2c), the aglycon of 10-deoxymethymycin (1c), has been accomplished in 16 steps and 12% overall yield from (S)-3-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (15c). The synthesis features an expeditious preparation of (+)-5a, a synthetic equivalent of the Prelog-Djerassi lactonic acid, and the construction of a 12-membered lactone through an intramolecular Nozaki-Hiyama-Kishi coupling reaction.