(2R,2'R,3R,3'R,4S,4'S,5R,5'R,6R,6'R)-6,6'-(propane-1,3-diyl)bis(2-methoxy-3,5-dimethyltetrahydro-2H-pyran-4-ol) | 1003273-38-8

• 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: (2R,2'R,3R,3'R,4S,4'S,5R,5'R,6R,6'R)-6,6'-(propane-1,3-diyl)bis(2-methoxy-3,5-dimethyltetrahydro-2H-pyran-4-ol)
• CAS: 1003273-38-8
• 化学式: C₁₉H₃₆O₆
• 分子量: 360.491
• InChiKey: KUYOOXNWFNBVTD-HHNMSUQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (2R,3S,5S,6R)-2-methoxy-6-[3-[(2R,3S,5S,6R)-6-methoxy-3,5-dimethyl-4-oxooxan-2-yl]propyl]-3,5-dimethyloxan-4-one 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到(2R,3R,4S,5R,6R)-2-(3-((2R,3R,4R,5R,6R)-4-hydroxy-6-methoxy-3,5-dimethyltetrahydro-2H-pyran-2-yl)propyl)-6-methoxy-3,5-dimethyltetrahydro-2H-pyran-4-ol
  参考文献：
  名称：

  A Two-Directional Approach to a (−)-Dictyostatin C11−C23 Segment:  Development of a Highly Diastereoselective, Kinetically-Controlled Meerwein−Ponndorf−Verley Reduction

  摘要：

  A three-step synthesis of a precursor to the C11-C23 segment of (-)-dictyostatin is described. The sequence features a sonication-assisted, enantioselective double hetero Diels-Alder (HDA) reaction catalyzed by Jacobsen's Cr(III) Schiff base catalyst, followed by a novel, highly diastereoselective Meerwein-Ponndorf-Verley (MPV) reduction of the hydropyranone subunits under kinetic control to yield the bis(axial alcohol) 4. Generalized studies of both the HDA and MPV methodologies are also described.

  DOI：

  10.1021/ja077336u