4-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((1E,5Z)-(R)-3-hydroxy-undeca-1,5-dienyl)-cyclopentyl]-butyric acid methyl ester | 248926-49-0

• 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: 4-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((1E,5Z)-(R)-3-hydroxy-undeca-1,5-dienyl)-cyclopentyl]-butyric acid methyl ester
• CAS: 248926-49-0
• 化学式: C₃₃H₆₄O₅Si₂
• 分子量: 597.039
• InChiKey: WEKWZLYSQIPGAV-VIQLPVMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.19
• 重原子数：
  40.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((1E,5Z)-(R)-3-hydroxy-undeca-1,5-dienyl)-cyclopentyl]-butyric acid methyl ester 在 氢氧化钾 、 potassium dihydrogenphosphate 、 四丁基氟化铵 作用下， 以 水 为溶剂， 生成 12-epiisoprostane-F_2α-V
  参考文献：
  名称：

  Synthesis of iPF2α-V: a new route

  摘要：

  We are reporting here on a new synthesis of iPF(2 alpha)-V, and we also disclose the first report on the synthesis of 12-epi-iPF(2 alpha)-V. The new total synthesis of iPF(2 alpha)-V reported here is designed to address metabolism and analytical issues. We have used this new route and also performed the total synthesis of 17,17,18,18-tetradeutero-iPF(2 alpha)-V. The availability of the deuterated analog of iPF(2 alpha)-V is the first step in our attempt to quantitate this isoprostane in biological fluids by GC and LC-MS. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01144-2
• 作为产物：
  描述：

  (4aS,5S,7R,7aS)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-3-one 在 palladium on activated charcoal 草酰氯 、 (R)-BINAL-H 、 氢气 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 4-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((1E,5Z)-(R)-3-hydroxy-undeca-1,5-dienyl)-cyclopentyl]-butyric acid methyl ester
  参考文献：
  名称：

  Synthesis of iPF2α-V: a new route

  摘要：

  We are reporting here on a new synthesis of iPF(2 alpha)-V, and we also disclose the first report on the synthesis of 12-epi-iPF(2 alpha)-V. The new total synthesis of iPF(2 alpha)-V reported here is designed to address metabolism and analytical issues. We have used this new route and also performed the total synthesis of 17,17,18,18-tetradeutero-iPF(2 alpha)-V. The availability of the deuterated analog of iPF(2 alpha)-V is the first step in our attempt to quantitate this isoprostane in biological fluids by GC and LC-MS. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01144-2