(2S,3S,6R)-2-(furan-2-yl)-6-methoxy-3-methyloxan-4-one | 1003274-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (2S,3S,6R)-2-(furan-2-yl)-6-methoxy-3-methyloxan-4-one
• CAS: 1003274-49-4
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: BWUXFGHYDIWHJN-ONOSFVFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,6R)-2-(furan-2-yl)-6-methoxy-3-methyloxan-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79%的产率得到(2S,3R,4S,6R)-2-(furan-2-yl)-6-methoxy-3-methyloxan-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
• 作为产物：
  描述：

  在 吡啶 、 氢氟酸 作用下， 以 甲醇 为溶剂， 生成 (2S,3S,6R)-2-(furan-2-yl)-6-methoxy-3-methyloxan-4-one
  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