tert-butyl((2R,3R,4R,5R)-2-methoxy-4-(2-(4-methoxybenzyloxy)ethyl)-5-vinyltetrahydrofuran-3-yloxy)dimethylsilane | 1133094-78-6

• 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: tert-butyl((2R,3R,4R,5R)-2-methoxy-4-(2-(4-methoxybenzyloxy)ethyl)-5-vinyltetrahydrofuran-3-yloxy)dimethylsilane
• 英文别名: tert-butyl-[(2R,3R,4R,5R)-5-ethenyl-2-methoxy-4-[2-[(4-methoxyphenyl)methoxy]ethyl]oxolan-3-yl]oxy-dimethylsilane
• CAS: 1133094-78-6
• 化学式: C₂₃H₃₈O₅Si
• 分子量: 422.637
• InChiKey: WYZQDLFNABQOOU-GXRSIYKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  tert-butyl((2R,3R,4R,5R)-2-methoxy-4-(2-(4-methoxybenzyloxy)ethyl)-5-vinyltetrahydrofuran-3-yloxy)dimethylsilane 在 正丁基锂 、 二氯二茂锆 、 三氟化硼乙醚 作用下， 以 正己烷 、 甲苯 为溶剂， 以86%的产率得到(1R,2R,3R,4R)-2-(tert-butyldimethylsilyloxy)-3-(2-(4-methoxybenzyloxy)ethyl)-4-vinylcyclobutanol
  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：

  (2R,3R,4S,5R)-2-methoxy-4-(2-(4-methoxybenzyloxy)ethyl)-5-vinyltetrahydrofuran-3-ol 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到tert-butyl((2R,3R,4R,5R)-2-methoxy-4-(2-(4-methoxybenzyloxy)ethyl)-5-vinyltetrahydrofuran-3-yloxy)dimethylsilane
  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.