(6S,7R,E)-7-hydroxy-3-methyl-6,8-diphenylmethoxy-2-octanoic acid ethyl ester | 223575-56-2

• 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: (6S,7R,E)-7-hydroxy-3-methyl-6,8-diphenylmethoxy-2-octanoic acid ethyl ester
• 英文别名: ethyl (E,6S,7R)-7-hydroxy-3-methyl-6,8-bis(phenylmethoxy)oct-2-enoate
• CAS: 223575-56-2
• 化学式: C₂₅H₃₂O₅
• 分子量: 412.526
• InChiKey: ZQHMBRHJUHGTJI-LQUDEKPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 (6S,7R,E)-7-hydroxy-3-methyl-6,8-diphenylmethoxy-2-octanoic acid ethyl ester 、 碘甲烷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 (1S,2S,3S)-1-methyl-3-phenylmethoxy-2-phenylmethoxymethylcyclopentaveacetic acid ethyl ester 、 (1R,2S,3S)-1-methyl-3-phenylmethoxy-2-phenylmethoxymethylcyclopentaneacetic acid ethyl ester 、
  参考文献：
  名称：

  Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center

  摘要：

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.

  DOI：

  10.1021/jo9822380
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium tetrahydroborate 、 草酰氯 、 三氟化硼乙醚 、 甲基锂 、 氢气 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 115.5h， 生成 (6S,7R,E)-7-hydroxy-3-methyl-6,8-diphenylmethoxy-2-octanoic acid ethyl ester
  参考文献：
  名称：

  Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center

  摘要：

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.

  DOI：

  10.1021/jo9822380

文献信息

• Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center
  作者：Qiang Zhu、Li-Xin Qiao、Yikang Wu、Yu-Lin Wu

  DOI：10.1021/jo9822380

  日期：1999.4.1

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.