(1R,4S,5S,1'R,2'R,5'R)-5-<<2'-<1''-<(benzyloxy)methyl>ethenyl>-5'-methylcyclopentyl>methyl>-5-(methoxymethyl)cyclopent-2-ene-1,4-dicarboxylic acid 1-methyl ester | 133349-44-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,4S,5S,1'R,2'R,5'R)-5-<<2'-<1''-<(benzyloxy)methyl>ethenyl>-5'-methylcyclopentyl>methyl>-5-(methoxymethyl)cyclopent-2-ene-1,4-dicarboxylic acid 1-methyl ester
• CAS: 133349-44-7
• 化学式: C₂₇H₃₆O₆
• 分子量: 456.579
• InChiKey: ZSHRHWMCNJETLI-QMRJUQCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,4S,5S,1'R,2'R,5'R)-5-<<2'-<1''-<(benzyloxy)methyl>ethenyl>-5'-methylcyclopentyl>methyl>-5-(methoxymethyl)cyclopent-2-ene-1,4-dicarboxylic acid 1-methyl ester 在 吡啶 、 lead(IV) acetate 、 copper diacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 38.5h， 生成 methyl 17-(benzyloxy)-19-methoxy-14,15,16-trisnorsordaric-1-en-18-oate
  参考文献：
  名称：

  Studies on the synthesis of the diterpenoid mold metabolite sordaricin. Exploration of a prospective biogenetic intramolecular [4 + 2] cycloaddition

  摘要：

  In a model study directed toward the synthesis of the diterpenoid sordaricin 3, the main carbon skeleton was established via intramolecular [4 + 2] cycloadditions of the 5,5-cyclopentadienyl derivatives 24 and 30. These intermediates were prepared by two similar routes, beginning with the alkylation of either the norbornenyl ester 14 or its enantiomer with iodide 16. The oxygenated two-carbon bridge in each of the resulting adducts was then cut away by a sequence of oxidative processes to form the diene component for the cycloadditions. For 24 this began with the Bayer-Villiger oxidation (21 --> 22) and for 30, Vedejs alpha-hydroxylation of 27, followed by periodate cleavage. In the latter case, the benzyloxy group was introduced into the dienophile moiety by selective epoxidation of the isopropenyl group followed by amide-initiated elimination.

  DOI：

  10.1021/jo00011a027
• 作为产物：
  描述：

  重氮甲烷 、 (1R,4S,7S,1'R,2'R,5'R)-7-<<2'-<1''-<(benzyloxy)methyl>ethenyl>-5'-methylcyclopentyl>methyl>-3-hydroxy-7-(methoxymethyl)bicyclo<2.2.1>hept-5-en-2-one 生成 (1R,4S,5S,1'R,2'R,5'R)-5-<<2'-<1''-<(benzyloxy)methyl>ethenyl>-5'-methylcyclopentyl>methyl>-5-(methoxymethyl)cyclopent-2-ene-1,4-dicarboxylic acid 1-methyl ester
  参考文献：
  名称：

  Studies on the synthesis of the diterpenoid mold metabolite sordaricin. Exploration of a prospective biogenetic intramolecular [4 + 2] cycloaddition

  摘要：

  In a model study directed toward the synthesis of the diterpenoid sordaricin 3, the main carbon skeleton was established via intramolecular [4 + 2] cycloadditions of the 5,5-cyclopentadienyl derivatives 24 and 30. These intermediates were prepared by two similar routes, beginning with the alkylation of either the norbornenyl ester 14 or its enantiomer with iodide 16. The oxygenated two-carbon bridge in each of the resulting adducts was then cut away by a sequence of oxidative processes to form the diene component for the cycloadditions. For 24 this began with the Bayer-Villiger oxidation (21 --> 22) and for 30, Vedejs alpha-hydroxylation of 27, followed by periodate cleavage. In the latter case, the benzyloxy group was introduced into the dienophile moiety by selective epoxidation of the isopropenyl group followed by amide-initiated elimination.

  DOI：

  10.1021/jo00011a027