(2R,3R,4S,5R,6S)-2-methoxy-3,5-dimethyl-6-phenyloxan-4-ol | 1003273-58-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-2-methoxy-3,5-dimethyl-6-phenyloxan-4-ol
• CAS: 1003273-58-2
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: PCERNZHAUVOVSL-SJVBDLOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,3R,5R,6R)-2-methoxy-3,5-dimethyl-6-phenyloxan-4-one 、 硼氢化钠 生成 (2R,3R,4S,5R,6S)-2-methoxy-3,5-dimethyl-6-phenyloxan-4-ol
  参考文献：
  名称：

  DANISHEFSKY, S.;LANGER, M. E., J. ORG. CHEM., 1985, 50, N 19, 3672-3674

  摘要：

  DOI：

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.