(2S,3R,4S,6S)-2-(furan-2-yl)-3,6-dimethyloxan-4-ol | 1003275-01-1

• 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: (2S,3R,4S,6S)-2-(furan-2-yl)-3,6-dimethyloxan-4-ol
• CAS: 1003275-01-1
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: NXWMTNUJFMJJKM-DKIAZLNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,3S,6S)-2-Furan-2-yl-3,6-dimethyl-tetrahydro-pyran-4-one 在 二苯甲醇 、 三甲基铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以73%的产率得到(2S,3R,4S,6S)-2-(furan-2-yl)-3,6-dimethyloxan-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

文献信息

• A Two-Directional Approach to a (−)-Dictyostatin C11−C23 Segment:  Development of a Highly Diastereoselective, Kinetically-Controlled Meerwein−Ponndorf−Verley Reduction
  作者：Andrew K. Dilger、Vijay Gopalsamuthiram、Steven D. Burke

  DOI：10.1021/ja077336u

  日期：2007.12.1

  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.