1,2-O-isopropylidene-3-C-(4-methoxyphenylethynyl)-α-D-allofuranose | 896130-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2-O-isopropylidene-3-C-(4-methoxyphenylethynyl)-α-D-allofuranose
• 英文别名: (1R)-1-[(3aR,5R,6R,6aR)-6-hydroxy-6-[2-(4-methoxyphenyl)ethynyl]-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
• CAS: 896130-25-9
• 化学式: C₁₈H₂₂O₇
• 分子量: 350.368
• InChiKey: HWSUDSBFAYHSHM-XLKGFZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-C-(4-methoxyphenylethynyl)-α-D-allofuranose 在 双(乙腈)氯化钯(II) 作用下， 以 乙腈 为溶剂， 以82%的产率得到1,2-O-isopropylidene-3-C-[2'-oxo-2'-(4-methoxyphenyl)ethyl]-α-D-allofuranose-(2'-C,5-O,6-O)-ketal
  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：

  3-C-ethynyl-1,2;5,6-di-O-isopropylidene-α-D-allo-hexofuranose 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 硫酸 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 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

文献信息

• The influence of electronic factors on palladium-mediated cycloisomerization: a systematic investigation of competitive 5-exo-dig versus 6-endo-dig cyclizations of sugar alkynols
  作者：C.V. Ramana、Rosy Mallik、Rajesh G. Gonnade

  DOI：10.1016/j.tet.2007.10.072

  日期：2008.1

  Pd-mediated cycloisomerization of 3-C-alkynyl-allo- and ribofuranose derivatives was investigated in detail to understand the influence of electronic factors on the regioselectivity in ring closure reaction. The reactions in general are influenced by the electronic nature of the substituent on the alkyne unit. A preference for endo-dig cyclization over exo-dig is noted, if the alkynyl substituent is not sufficiently electron withdrawing, (c) 2007 Elsevier Ltd. All rights reserved.