(+)-{5-[2-[6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl]-ethyl]-5,6,8a-trimethyl-decahydronaphthalen-1-yl 6'-(tert-butoxycarbonyl)amino-hexanoate} | 753002-54-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-{5-[2-[6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl]-ethyl]-5,6,8a-trimethyl-decahydronaphthalen-1-yl 6'-(tert-butoxycarbonyl)amino-hexanoate}
• 英文别名: [(1R,4aR,5S,6S,8aR)-5-[2-[(2R)-2-(furan-3-yl)-3,6-dihydro-2H-pyran-5-yl]ethyl]-5,6,8a-trimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl] 6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 753002-54-9
• 化学式: C₃₅H₅₅NO₆
• 分子量: 585.825
• InChiKey: CTAWRUVPBODYEK-PBKTUBKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-{5-[2-[6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl]-ethyl]-5,6,8a-trimethyl-decahydronaphthalen-1-yl 6'-(tert-butoxycarbonyl)amino-hexanoate} 在 氧气 、 rose bengal 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到(+)-{5-[2-[6-(2-hydroxy-5-oxo-2,5-dihydro-furan-3-yl)-5,6-dihydro-2H-pyran-3-yl]-ethyl]-5,6,8a-trimethyl-decahydronaphthalen-1-yl 6'-(tert-butoxycarbonyl)amino-hexanoate}
  参考文献：
  名称：

  Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition

  摘要：

  The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the gamma-hydroxybutenolide moiety.

  DOI：

  10.1021/jo049285e
• 作为产物：
  描述：

  3-糠醛 在 Grubbs catalyst first generation 、 di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium 盐酸 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium tetrahydroborate 、 乙醇 、 氨 、 氢气 、 lithium 、 sodium hydride 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N'-二异丙基碳二亚胺 、 叔丁醇 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， -78.0~75.0 ℃ 、303.98 kPa 条件下， 反应 235.5h， 生成 (+)-{5-[2-[6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl]-ethyl]-5,6,8a-trimethyl-decahydronaphthalen-1-yl 6'-(tert-butoxycarbonyl)amino-hexanoate}
  参考文献：
  名称：

  Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition

  摘要：

  The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the gamma-hydroxybutenolide moiety.

  DOI：

  10.1021/jo049285e