4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl ester | 185114-44-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl ester
• 英文别名: [(1S,2R,3S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2-(2-oxoethyl)-3-(phenylmethoxymethoxy)cyclopentyl]methyl 4-bromobenzoate
• CAS: 185114-44-7
• 化学式: C₂₉H₃₉BrO₆Si
• 分子量: 591.615
• InChiKey: WYEKIRBXGMFQEV-XDZXDJIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl ester 在 Pd-BaSO₄ chromium(VI) oxide 、 六甲基磷酰三胺 、 正丁基锂 、 硫酸 、 氢气 、 二异丁基氢化铝 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 作用下， 以 六甲基磷酰三胺 为溶剂， 生成 (Z,4S)-4-[tert-butyl(dimethyl)silyl]oxy-7-[(1R,2R,3S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2-[(Z)-oct-2-enyl]-3-(phenylmethoxymethoxy)cyclopentyl]hept-5-enoic acid
  参考文献：
  名称：

  New marine prostanoids, preclavulone lactones, from the Okinawan soft coral Clavularia viridis

  摘要：

  Two new marine prostanoids, preclavulone lactones I (1) and II (2) were isolated from the Okinawan soft coral, Clavularia viridis. Their structures were determined based on spectroscopic analysis and chemical synthesis from (S)-malic acid. Preclavulone Lactones with side chains having absolute configurations opposite to those of mammalian prostanoids could be recognized as key intermediates in biosynthesis of clavulones. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10211-8
• 作为产物：
  描述：

  4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentylmethyl ester 在 pyridine-SO3 complex 、 (Sia)2BH 、 二甲基亚砜 、 三乙胺 作用下， 以94%的产率得到4-Bromo-benzoic acid (1S,2R,3S,5S)-3-benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-cyclopentylmethyl ester
  参考文献：
  名称：

  New marine prostanoids, preclavulone lactones, from the Okinawan soft coral Clavularia viridis

  摘要：

  Two new marine prostanoids, preclavulone lactones I (1) and II (2) were isolated from the Okinawan soft coral, Clavularia viridis. Their structures were determined based on spectroscopic analysis and chemical synthesis from (S)-malic acid. Preclavulone Lactones with side chains having absolute configurations opposite to those of mammalian prostanoids could be recognized as key intermediates in biosynthesis of clavulones. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10211-8

文献信息

• New marine prostanoids, preclavulone lactones, from the Okinawan soft coral Clavularia viridis
  作者：Makoto Iwashima、Kinzo Watanabe、Kazuo Iguchi

  DOI：10.1016/s0040-4039(97)10211-8

  日期：1997.12

  Two new marine prostanoids, preclavulone lactones I (1) and II (2) were isolated from the Okinawan soft coral, Clavularia viridis. Their structures were determined based on spectroscopic analysis and chemical synthesis from (S)-malic acid. Preclavulone Lactones with side chains having absolute configurations opposite to those of mammalian prostanoids could be recognized as key intermediates in biosynthesis of clavulones. (C) 1997 Elsevier Science Ltd.