(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 | 159697-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (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
• CAS: 159697-96-8
• 化学式: C₂₀H₄₀O₄Si₂
• 分子量: 400.706
• InChiKey: LLAOBGGFQPIRLJ-VVLHAWIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 草酰氯 、 potassium tert-butylate 、 水 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.08h， 生成 (Z)-7-[(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((E)-3-oxo-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid methyl ester
  参考文献：
  名称：

  Hwang, Seong Woo; Adiyaman, Mustafa; Khanapure, Subhash, Journal of the American Chemical Society, 1994, vol. 116, # 23, p. 10829 - 10830

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (E,4S,6R)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[(4S)-2-sulfanylidene-1,3-dioxolan-4-yl]hex-2-enoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 5.0h， 以52%的产率得到(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
  参考文献：
  名称：

  iPF2α-III metabolism. First total synthesis of 2,3-dinor iPF2α-III, a primary β-oxidation metabolite

  摘要：

  The total synthesis of a primary iPF(2 alpha)-III metabolite, namely dinor iPF(2 alpha)-III 8, is described. The successful synthesis was finally accomplished by generating the carboxylic acid group at the end of the synthesis so as to avoid formation of an alpha,beta -unsaturated carboxylic acid, which is prone to undergo side reactions (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01794-4

文献信息

• Stereocontrolled Access to Isoprostanes via a Bicyclo[3.3.0]octene Framework
  作者：Camille Oger、Yasmin Brinkmann、Samira Bouazzaoui、Thierry Durand、Jean-Marie Galano

  DOI：10.1021/ol802104z

  日期：2008.11.6

  stereocontrolled strategy toward the total synthesis of isoprostanes based on a bicyclic alpha,beta-epoxy ketone intermediate 6. Bicyclo[3.3.0]octene scaffold permitted stereodirection of reagents allowing stereoselective epoxidation, diastereoselective ketone reduction, and regioselective epoxide opening otherwise not accessible with a simple cyclopentene framework.

  我们报告了基于双环α，β-环氧酮中间体6的异丙醇全合成的简单且高度立体控制的策略。双环[3.3.0]辛烯骨架允许试剂的立体定向，从而允许立体选择性环氧化，非对映选择性酮还原和区域选择性环氧化物否则无法通过简单的环戊烯框架打开。
• The Isoprostanes, A New Class of Natural Products: Synthesis and Biosynthesis
  作者：Joshua Rokach

  DOI：10.1055/s-1998-5926

  日期：1998.3
• iPF2α-III-17,18,19,20-d4: Total synthesis and metabolism
  作者：Seongjin Kim、William S. Powell、John A. Lawson、Sheila H. Jacobo、Domenico Pratico、Garret A. FitzGerald、Kirk Maxey、Joshua Rokach

  DOI：10.1016/j.bmcl.2005.01.062

  日期：2005.3

  The first total synthesis of 17,18,19,20-d(4)-iPF(2 alpha)-III 32, a deuterated analog of iPF(2 alpha)-III is described. We have used this analog in some beta-oxidation studies with rat liver homogenates and have shown that 32 was metabolized to 17,18,19,20-tetradeutero2,3-dinor-iPF(2 alpha)-III 36 and 17,18,19,20-tetradeutero-2,3-dinor-5,6-dihydro-iPF(2 alpha)-III 37. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.
• Hwang, Seong Woo; Adiyaman, Mustafa; Khanapure, Subhash, Journal of the American Chemical Society, 1994, vol. 116, # 23, p. 10829 - 10830
  作者：Hwang, Seong Woo、Adiyaman, Mustafa、Khanapure, Subhash、Schio, Laurent、Rokach, Joshua

  DOI：——

  日期：——