(1R)-1-[(3aR,5R,6S,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 | 945624-85-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1R)-1-[(3aR,5R,6S,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: 945624-85-1
• 化学式: C₁₈H₂₂O₇
• 分子量: 350.368
• InChiKey: HWSUDSBFAYHSHM-QFXBJFAPSA-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：

  (1R)-1-[(3aR,5R,6S,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 在 双(乙腈)氯化钯(II) 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以62%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：

  Steric control in Pd-mediated cycloisomerization of sugar alkynols: documentation of a rare allylic epimerization

  摘要：

  Pd-mediated cycloisomerization of C3-alkynylated glucofuranosyl derivatives revealed a dominance of steric factors over electronic factors. However, the intermediate glycals were epimerized prior to the ketalization and afforded the more stable cis-fused bicyclic ketals. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.133
• 作为产物：
  描述：

  (Z)-3-deoxy-3-C-[(hydroxymethyl)methylene]-1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 四氯化碳 、 正丁基锂 、 硫酸 、 碳酸氢钠 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 (1R)-1-[(3aR,5R,6S,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
  参考文献：
  名称：

  Steric control in Pd-mediated cycloisomerization of sugar alkynols: documentation of a rare allylic epimerization

  摘要：

  Pd-mediated cycloisomerization of C3-alkynylated glucofuranosyl derivatives revealed a dominance of steric factors over electronic factors. However, the intermediate glycals were epimerized prior to the ketalization and afforded the more stable cis-fused bicyclic ketals. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.133

文献信息

• Steric control in Pd-mediated cycloisomerization of sugar alkynols: documentation of a rare allylic epimerization
  作者：C.V. Ramana、Pitambar Patel、Rajesh G. Gonnade

  DOI：10.1016/j.tetlet.2007.04.133

  日期：2007.7

  Pd-mediated cycloisomerization of C3-alkynylated glucofuranosyl derivatives revealed a dominance of steric factors over electronic factors. However, the intermediate glycals were epimerized prior to the ketalization and afforded the more stable cis-fused bicyclic ketals. (c) 2007 Elsevier Ltd. All rights reserved.