(3aR,5R,6R,6aR)-6-(2-(4-methoxybenzyloxy)ethyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole | 1133094-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aR,5R,6R,6aR)-6-(2-(4-methoxybenzyloxy)ethyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole
• 英文别名: (3aR,5R,6R,6aR)-5-ethenyl-6-[2-[(4-methoxyphenyl)methoxy]ethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 1133094-74-2
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: DQVMMPKZBQKANN-BRSBDYLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 (3aR,5R,6R,6aR)-6-(2-(4-methoxybenzyloxy)ethyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole 在 盐酸 作用下， 反应 16.0h， 以62%的产率得到(2R,3R,4S,5R)-2-methoxy-4-(2-(4-methoxybenzyloxy)ethyl)-5-vinyltetrahydrofuran-3-ol
  参考文献：
  名称：

  Synthesis of the Cyclobutylfuran Sector of Providencin via Zirconium-mediated Oxygen Abstraction from a Furanoside

  摘要：

  A portion of the macrocyclic cembrenoid diterpene providencin possessing conjoined cyclobutane and furancarboxylate units was synthesized from D-glucose using deoxygenative ring contraction methodology to construct the tetrasubstituted cyclobutane and a Knoevenagel condensation of glyceraldehyde to fabricate the trisubstituted furan.

  DOI：

  10.1021/ol900152p
• 作为产物：
  描述：

  (S)-1-((3aR,5S,6R,6aR)-6-(2-(4-methoxybenzyloxy)ethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以94%的产率得到(3aR,5R,6R,6aR)-6-(2-(4-methoxybenzyloxy)ethyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole
  参考文献：
  名称：

  Synthesis of the Cyclobutylfuran Sector of Providencin via Zirconium-mediated Oxygen Abstraction from a Furanoside

  摘要：

  A portion of the macrocyclic cembrenoid diterpene providencin possessing conjoined cyclobutane and furancarboxylate units was synthesized from D-glucose using deoxygenative ring contraction methodology to construct the tetrasubstituted cyclobutane and a Knoevenagel condensation of glyceraldehyde to fabricate the trisubstituted furan.

  DOI：

  10.1021/ol900152p

文献信息

• Synthesis of the Cyclobutylfuran Sector of Providencin via Zirconium-mediated Oxygen Abstraction from a Furanoside
  作者：James D. White、Somnath Jana

  DOI：10.1021/ol900152p

  日期：2009.3.19

  A portion of the macrocyclic cembrenoid diterpene providencin possessing conjoined cyclobutane and furancarboxylate units was synthesized from D-glucose using deoxygenative ring contraction methodology to construct the tetrasubstituted cyclobutane and a Knoevenagel condensation of glyceraldehyde to fabricate the trisubstituted furan.