methyl (αR,βR,2S,3S,3'aS,4S,5'R)-α,3-dimethyl-α-ethyl-3',3'a,4,5,5',6'-hexahydro-β-hydroxy-3-methyl-5'-pentyl-8'-(2-propenyloxy)-9'-(2-propenyloxycarbonyl)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-4-butanoate | 1141365-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl (αR,βR,2S,3S,3'aS,4S,5'R)-α,3-dimethyl-α-ethyl-3',3'a,4,5,5',6'-hexahydro-β-hydroxy-3-methyl-5'-pentyl-8'-(2-propenyloxy)-9'-(2-propenyloxycarbonyl)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-4-butanoate
• 英文别名: prop-2-enyl (3S,3'S,4'S,5S,7R)-4'-[(2R,3R)-2-hydroxy-3-methoxycarbonyl-3-methylpentyl]-3'-methyl-7-pentyl-11-prop-2-enoxyspiro[2,6-dioxatricyclo[7.3.1.05,13]trideca-1(13),9,11-triene-3,2'-oxolane]-12-carboxylate
• CAS: 1141365-52-7
• 化学式: C₃₅H₅₀O₉
• 分子量: 614.777
• InChiKey: GRRZZTSYCBENPE-VWSUHBNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (αR,βR,2S,3S,3'aS,4S,5'R)-α,3-dimethyl-α-ethyl-3',3'a,4,5,5',6'-hexahydro-β-hydroxy-3-methyl-5'-pentyl-8'-(2-propenyloxy)-9'-(2-propenyloxycarbonyl)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-4-butanoate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到methyl (αR,2S,3S,3'aS,4S,5'R)-α,3-dimethyl-α-ethyl-3',3'a,4,5,5',6'-hexahydro-3-methyl-β-oxo-5'-pentyl-8'-(2-propenyloxy)-9'-(2-propenyloxycarbonyl)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-4-butanoate
  参考文献：
  名称：

  Synthesis of (−)-Berkelic Acid

  摘要：

  AbstractAn extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6‐dihydroxybenzoic acid is the key step in the synthesis of (−)‐berkelic acid confirming Fürstner's reassignment of the stereochemistry at C18 and C19, establishing the absolute stereochemistry, and tentatively assigning the stereochemistry at C22.magnified image

  DOI：

  10.1002/anie.200805488
• 作为产物：
  描述：

  2-propenyl (2S,3S,3'aS,4S,5'R)-3',3'a,4,5,5',6'-hexahydro-3-methyl-4-[2-oxoethyl]-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate 、 1-methoxy-1-trimethylsiloxy-2-methyl-1-butene 在 N-(p-toluenesulfonyl)-L-valine 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.18h， 以40%的产率得到methyl (αS,βR,2S,3S,3'aS,4S,5'R)-α,3-dimethyl-α-ethyl-3',3'a,4,5,5',6'-hexahydro-β-hydroxy-3-methyl-5'-pentyl-8'-(2-propenyloxy)-9'-(2-propenyloxycarbonyl)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-4-butanoate
  参考文献：
  名称：

  Synthesis of (−)-Berkelic Acid

  摘要：

  AbstractAn extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6‐dihydroxybenzoic acid is the key step in the synthesis of (−)‐berkelic acid confirming Fürstner's reassignment of the stereochemistry at C18 and C19, establishing the absolute stereochemistry, and tentatively assigning the stereochemistry at C22.magnified image

  DOI：

  10.1002/anie.200805488

文献信息

• Synthesis of (−)-Berkelic Acid
  作者：Xiaoxing Wu、Jingye Zhou、Barry B. Snider

  DOI：10.1002/anie.200805488

  日期：2009.2.2

  AbstractAn extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6‐dihydroxybenzoic acid is the key step in the synthesis of (−)‐berkelic acid confirming Fürstner's reassignment of the stereochemistry at C18 and C19, establishing the absolute stereochemistry, and tentatively assigning the stereochemistry at C22.magnified image