(2R,4S,5R)-4-((S)-3-chloro-1-hydroxybut-3-en-1-yl)-2-phenyl-1,3-dioxan-5-ol | 1179318-61-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2R,4S,5R)-4-((S)-3-chloro-1-hydroxybut-3-en-1-yl)-2-phenyl-1,3-dioxan-5-ol
• CAS: 1179318-61-6
• 化学式: C₁₄H₁₇ClO₄
• 分子量: 284.74
• InChiKey: VHKFIHFJQZUCEN-RFQIPJPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R)-4-((S)-3-chloro-1-hydroxybut-3-en-1-yl)-2-phenyl-1,3-dioxan-5-ol 、 triphenylindium 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 (2R,4S,5R)-4-[(1S)-1-hydroxy-3-phenylbut-3-enyl]-2-phenyl-1,3-dioxan-5-ol
  参考文献：
  名称：

  A Sequential Indium-Mediated Aldehyde Allylation/Palladium-Catalyzed Cross-Coupling Reaction in the Synthesis of 2-Deoxy-β-C-Aryl Glycosides

  摘要：

  Indium-mediated allylation of aldehydes with 2-chloro-3-iodopropene, followed by a palladium-catalyzed cross-coupling reaction with triarylindium reagents or arylboronic acids, leads to aryl-substituted homoallylic alcohols in good to excellent yields and diastereoselectivities. The products obtained from reactions conducted with D-glyceraldehyde acetonide can be transformed into 2-deoxy-beta-C-aryl ribofuranosides in high overall yields. Similarly, 2-deoxy-beta-C-aryl allopyranosides may be prepared efficiently from 2,4-O-benzylidene erythrose.

  DOI：

  10.1021/ol901353f
• 作为产物：
  描述：

  2-氯-3-碘丙-1-烯 、 2,4-O-苄叉-D-赤藓糖 在 indium 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以78%的产率得到(2R,4S,5R)-4-((S)-3-chloro-1-hydroxybut-3-en-1-yl)-2-phenyl-1,3-dioxan-5-ol
  参考文献：
  名称：

  A Sequential Indium-Mediated Aldehyde Allylation/Palladium-Catalyzed Cross-Coupling Reaction in the Synthesis of 2-Deoxy-β-C-Aryl Glycosides

  摘要：

  Indium-mediated allylation of aldehydes with 2-chloro-3-iodopropene, followed by a palladium-catalyzed cross-coupling reaction with triarylindium reagents or arylboronic acids, leads to aryl-substituted homoallylic alcohols in good to excellent yields and diastereoselectivities. The products obtained from reactions conducted with D-glyceraldehyde acetonide can be transformed into 2-deoxy-beta-C-aryl ribofuranosides in high overall yields. Similarly, 2-deoxy-beta-C-aryl allopyranosides may be prepared efficiently from 2,4-O-benzylidene erythrose.

  DOI：

  10.1021/ol901353f