methyl 3-((1R,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2-(2-(4-methoxybenzyloxy)ethyl)-4-(triisopropylsilyloxy)cyclobutyl)-3-oxopropanoate | 1133094-86-6

• 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: methyl 3-((1R,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2-(2-(4-methoxybenzyloxy)ethyl)-4-(triisopropylsilyloxy)cyclobutyl)-3-oxopropanoate
• 英文别名: methyl 3-[(1R,2R,3R,4R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[2-[(4-methoxyphenyl)methoxy]ethyl]-4-tri(propan-2-yl)silyloxycyclobutyl]-3-oxopropanoate
• CAS: 1133094-86-6
• 化学式: C₃₃H₅₈O₇Si₂
• 分子量: 622.99
• InChiKey: CNRSKLQGFONJTF-PNEQTXRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.93
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-((1R,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2-(2-(4-methoxybenzyloxy)ethyl)-4-(triisopropylsilyloxy)cyclobutyl)-3-oxopropanoate 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 生成
  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：

  氰基甲酸甲酯 、 1-((1R,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2-(2-(4-methoxybenzyloxy)ethyl)-4-(triisopropylsilyloxy)cyclobutyl)ethanone 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到methyl 3-((1R,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2-(2-(4-methoxybenzyloxy)ethyl)-4-(triisopropylsilyloxy)cyclobutyl)-3-oxopropanoate
  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.