methyl 2-((1R,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2-(2-(4-methoxybenzyloxy)ethyl)-4-(triisopropylsilyloxy)cyclobutyl)-5-formylfuran-3-carboxylate | 1133094-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: methyl 2-((1R,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2-(2-(4-methoxybenzyloxy)ethyl)-4-(triisopropylsilyloxy)cyclobutyl)-5-formylfuran-3-carboxylate
• 英文别名: methyl 2-[(1R,2R,3R,4R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[2-[(4-methoxyphenyl)methoxy]ethyl]-4-tri(propan-2-yl)silyloxycyclobutyl]-5-formylfuran-3-carboxylate
• CAS: 1133094-93-5
• 化学式: C₃₆H₅₈O₈Si₂
• 分子量: 675.023
• InChiKey: MXYXOTDPOCUJJP-MBUTWZNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.16
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-((1R,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2-(2-(4-methoxybenzyloxy)ethyl)-4-(triisopropylsilyloxy)cyclobutyl)-5-formylfuran-3-carboxylate 、 (1-重氮基-2-氧代丙基)膦酸二甲酯 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以81%的产率得到methyl 2-((1R,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2-(2-(4-methoxybenzyloxy)ethyl)-4-(triisopropylsilyloxy)cyclobutyl)-5-ethynylfuran-3-carboxylate
  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：

  methyl 2-((1R,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2-(2-(4-methoxybenzyloxy)ethyl)-4-(triisopropylsilyloxy)cyclobutyl)-5-(hydroxymethyl)furan-3-carboxylate 在 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以88%的产率得到methyl 2-((1R,2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2-(2-(4-methoxybenzyloxy)ethyl)-4-(triisopropylsilyloxy)cyclobutyl)-5-formylfuran-3-carboxylate
  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.