(4R,6R)-6-(((R)-5-hydroxytetrahydrofuran-2-yl)methyl)-4-methoxy-5,5-dimethyltetrahydro-2H-pyran-2-ol | 1083401-30-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (4R,6R)-6-(((R)-5-hydroxytetrahydrofuran-2-yl)methyl)-4-methoxy-5,5-dimethyltetrahydro-2H-pyran-2-ol
• 英文别名: (4R,6R)-6-[[(2R)-5-hydroxyoxolan-2-yl]methyl]-4-methoxy-5,5-dimethyloxan-2-ol
• CAS: 1083401-30-2
• 化学式: C₁₃H₂₄O₅
• 分子量: 260.331
• InChiKey: DRACOUPKBNVWOX-HVHKSXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 (4R,6R)-6-(((R)-5-hydroxytetrahydrofuran-2-yl)methyl)-4-methoxy-5,5-dimethyltetrahydro-2H-pyran-2-ol 在 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 (4R,6R)-4-methoxy-6-(((R)-5-methoxytetrahydrofuran-2-yl)methyl)-5,5-dimethyltetrahydro-2H-pyran-2-ol
  参考文献：
  名称：

  茶黄素 D 的全合成。

  摘要：

  The total synthesis of the potent cytotoxin theopederin D has been achieved through the use of an oxidative carbon–carbon bond cleavage reaction to form an acyliminium ion in the presence of acid labile acetal groups Other key transformations include an acid mediated functionalization of a tetrahydrofuranyl alcohol in the presence of a tetrahydropyranyl alcohol, a syn-selective glycal epoxide opening, and a catalytic asymmetric aldehyde-acid chloride condensation.

  DOI：

  10.1002/anie.200802548
• 作为产物：
  描述：

  (5R,7R,9R)-9-methoxy-8,8-dimethyldodeca-1,11-diene-5,7-diol 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以82%的产率得到(4R,6R)-6-(((R)-5-hydroxytetrahydrofuran-2-yl)methyl)-4-methoxy-5,5-dimethyltetrahydro-2H-pyran-2-ol
  参考文献：
  名称：

  茶黄素 D 的全合成。

  摘要：

  The total synthesis of the potent cytotoxin theopederin D has been achieved through the use of an oxidative carbon–carbon bond cleavage reaction to form an acyliminium ion in the presence of acid labile acetal groups Other key transformations include an acid mediated functionalization of a tetrahydrofuranyl alcohol in the presence of a tetrahydropyranyl alcohol, a syn-selective glycal epoxide opening, and a catalytic asymmetric aldehyde-acid chloride condensation.

  DOI：

  10.1002/anie.200802548

文献信息

• Total Synthesis of Theopederin D
  作者：Michael E. Green、Jason C. Rech、Paul E. Floreancig

  DOI：10.1002/anie.200802548

  日期：2008.9.8

  The total synthesis of the potent cytotoxin theopederin D has been achieved through the use of an oxidative carbon–carbon bond cleavage reaction to form an acyliminium ion in the presence of acid labile acetal groups Other key transformations include an acid mediated functionalization of a tetrahydrofuranyl alcohol in the presence of a tetrahydropyranyl alcohol, a syn-selective glycal epoxide opening, and a catalytic asymmetric aldehyde-acid chloride condensation.