4-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((1E,5Z)-(S)-3-hydroxy-undeca-1,5-dienyl)-cyclopentyl]-butyric acid methyl ester | 248926-47-8

• 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)-(S)-3-hydroxy-undeca-1,5-dienyl)-cyclopentyl]-butyric acid methyl ester
• 英文别名: methyl 4-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(1E,3S,5Z)-3-hydroxyundeca-1,5-dienyl]cyclopentyl]butanoate
• CAS: 248926-47-8
• 化学式: C₃₃H₆₄O₅Si₂
• 分子量: 597.039
• InChiKey: WEKWZLYSQIPGAV-WILMXUIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.19
• 重原子数：
  40
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  4-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((1E,5Z)-(S)-3-hydroxy-undeca-1,5-dienyl)-cyclopentyl]-butyric acid methyl ester 在 四丁基氟化铵 作用下， 以95%的产率得到methyl 4-<3α,5α-dihydroxy-2β-<(3S)-hydroxy-(E,Z)-1,5-undecadien>-1β-cyclopentane>butanoate
  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]-1,3,4,4a,5,6,7,7a-octahydrocyclopenta[c]pyran-3-ol 在 palladium on activated charcoal 草酰氯 、 (-)-(S)-BINAL-H 、 氢气 、 sodium hexamethyldisilazane 、 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)-(S)-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

文献信息

• Synthesis of iPF2α-V: a new route
  作者：Seong Woo Hwang、Mustafa Adiyaman、John A Lawson、Garret A FitzGerald、Joshua Rokach

  DOI：10.1016/s0040-4039(99)01144-2

  日期：1999.8

  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.