methyl 4-((1S,2R,3R,5S)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-((S,1E,5Z)-3-hydroxyundeca-1,5-dien-1-yl-8,8,9,9-d4)cyclopentyl)butanoate | 248926-64-9

• 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: methyl 4-((1S,2R,3R,5S)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-((S,1E,5Z)-3-hydroxyundeca-1,5-dien-1-yl-8,8,9,9-d4)cyclopentyl)butanoate
• CAS: 248926-64-9
• 化学式: C₃₃H₆₄O₅Si₂
• 分子量: 601.007
• InChiKey: WEKWZLYSQIPGAV-TZQCQUDNSA-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：

  methyl 4-((1S,2R,3R,5S)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-((S,1E,5Z)-3-hydroxyundeca-1,5-dien-1-yl-8,8,9,9-d4)cyclopentyl)butanoate 在 氢氟酸 作用下， 以 乙腈 为溶剂， 以88%的产率得到methyl 4-((1S,2R,3R,5S)-3,5-dihydroxy-2-((S,1E,5Z)-3-hydroxyundeca-1,5-dien-1-yl-8,8,9,9-d4)cyclopentyl)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]-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-3-one 在 palladium on activated charcoal 草酰氯 、 (-)-(S)-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 methyl 4-((1S,2R,3R,5S)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-((S,1E,5Z)-3-hydroxyundeca-1,5-dien-1-yl-8,8,9,9-d4)cyclopentyl)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