(3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-phenylethynyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol | 896130-21-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-phenylethynyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol
• 英文别名: (3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[2-(4-methoxyphenyl)ethynyl]-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-ol
• CAS: 896130-21-5
• 化学式: C₂₁H₂₆O₇
• 分子量: 390.433
• InChiKey: ZECYEMADEKAAQG-ZIKOTGLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-phenylethynyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 在 硫酸 作用下， 以 甲醇 为溶剂， 以80%的产率得到1,2-O-isopropylidene-3-C-(4-methoxyphenylethynyl)-α-D-allofuranose
  参考文献：
  名称：

  Palladium mediated cycloisomerization of sugar alkynols: synthesis of cyclic enol-ethers and spiroketals

  摘要：

  Functionalized bicyclic enol-ethers and spiroketals are prepared by Pd catalyzed cycloisomerization of 3-C-alkynylfuranosyl derivatives. Cycloisomerization of differently substituted alkyne derivatives revealed a preference for 6-endo-dig cyclization over 5-exo-dig if the substituent is not sufficiently electron withdrawing. The scope of these cycloisomerizations has been further extended by integrating with conjugate addition. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.143
• 作为产物：
  描述：

  4-碘苯甲醚 、 3-C-ethynyl-1,2;5,6-di-O-isopropylidene-α-D-allo-hexofuranose 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到(3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-phenylethynyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol
  参考文献：
  名称：

  Palladium mediated cycloisomerization of sugar alkynols: synthesis of cyclic enol-ethers and spiroketals

  摘要：

  Functionalized bicyclic enol-ethers and spiroketals are prepared by Pd catalyzed cycloisomerization of 3-C-alkynylfuranosyl derivatives. Cycloisomerization of differently substituted alkyne derivatives revealed a preference for 6-endo-dig cyclization over 5-exo-dig if the substituent is not sufficiently electron withdrawing. The scope of these cycloisomerizations has been further extended by integrating with conjugate addition. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.143

文献信息

• Palladium mediated cycloisomerization of sugar alkynols: synthesis of cyclic enol-ethers and spiroketals
  作者：C.V. Ramana、Rosy Mallik、Rajesh G. Gonnade、Mukund K. Gurjar

  DOI：10.1016/j.tetlet.2006.03.143

  日期：2006.5

  Functionalized bicyclic enol-ethers and spiroketals are prepared by Pd catalyzed cycloisomerization of 3-C-alkynylfuranosyl derivatives. Cycloisomerization of differently substituted alkyne derivatives revealed a preference for 6-endo-dig cyclization over 5-exo-dig if the substituent is not sufficiently electron withdrawing. The scope of these cycloisomerizations has been further extended by integrating with conjugate addition. (c) 2006 Elsevier Ltd. All rights reserved.