15(RS)-9,11-O-di(triethylsilyl)-5,6-dehydro-8-epi-PGF_2α methyl ester | 188255-18-7

• 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: 15(RS)-9,11-O-di(triethylsilyl)-5,6-dehydro-8-epi-PGF_2α methyl ester
• 英文别名: methyl 7-[(1S,2R,3R,5S)-2-[(E)-3-hydroxyoct-1-enyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hept-5-ynoate
• CAS: 188255-18-7
• 化学式: C₃₃H₆₂O₅Si₂
• 分子量: 595.023
• InChiKey: XDPMBOZRDYEBDU-COUXNCEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.64
• 重原子数：
  40
• 可旋转键数：
  21
• 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：

  15(RS)-9,11-O-di(triethylsilyl)-5,6-dehydro-8-epi-PGF_2α methyl ester 在 sodium tetrahydroborate 、 Pd-BaSO₄ 、 lead acetate sodium hydroxide 、 超重氢 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 水 为溶剂， 20.0 ℃ 、40.0 kPa 条件下， 反应 5.5h， 生成 15(R)-[5,6-3H2]-8-epi-PGF_2α
  参考文献：
  名称：

  Synthesis of labelled oxylipins: leukotriene A4 and 8-epi-prostaglandin F2α

  摘要：

  Tritiated leukotriene A(4) and 8-epi-prostaglandin F-2 alpha methyl esters were prepared from the corresponding acetylenic precursors by selective reduction with tritium gas to provide a probe for the metabolite identification of these oxylipins. Partially deactivated Pd-catalysts were prepared from commercial products and their composition was optimized to achieve the better selectivity. A micro-method for the saponification of labelled oxylipins methyl esters was used.

  DOI：

  10.1002/(sici)1099-1344(199907)42:7<663::aid-jlcr228>3.0.co;2-k
• 作为产物：
  描述：

  methyl (9S,11R,12E,14Z)-8-iodo-9,11-bis(triethylsilyloxy)icosa-12,14-dien-5-ynoate 在 三苯基膦 三乙基硼 、 氧气 、 三正丁基氢锡 作用下， 以 xylene 为溶剂， 反应 0.5h， 以55%的产率得到15(RS)-9,11-O-di(triethylsilyl)-5,6-dehydro-8-epi-PGF_2α methyl ester
  参考文献：
  名称：

  Synthesis of labelled oxylipins: leukotriene A4 and 8-epi-prostaglandin F2α

  摘要：

  Tritiated leukotriene A(4) and 8-epi-prostaglandin F-2 alpha methyl esters were prepared from the corresponding acetylenic precursors by selective reduction with tritium gas to provide a probe for the metabolite identification of these oxylipins. Partially deactivated Pd-catalysts were prepared from commercial products and their composition was optimized to achieve the better selectivity. A micro-method for the saponification of labelled oxylipins methyl esters was used.

  DOI：

  10.1002/(sici)1099-1344(199907)42:7<663::aid-jlcr228>3.0.co;2-k

文献信息

• Total Synthesis of (15<i>R</i>)- and (15<i>S</i>)-F_2t-Isoprostanes by a Biomimetic Process Using the Cyclization of Acyclic Dihydroxylated Octa-5,7-dienyl Radicals
  作者：Thierry Durand、Alexandre Guy、Jean-Pierre Vidal、Jean-Claude Rossi

  DOI：10.1021/jo0109624

  日期：2002.5.1

  We report a new route to F-2t-IsoP (formerly named 8-epi-PGF(2alpha)) using a biomimetic radical cyclization of a highly functionalized C20 precursor. The strategy employed gives a beta-hydroxy free radical followed by molecular oxygen trapping, which is an unusual method for quenching carbon free radicals. We observed the formation of unique diastereoisomers (15R)- and (15S)-F-2t-IsoP. This result is consistent with a strong stereoelectronic control associated with a steric effect initiated by the side chains alpha and omega on the cyclopentane ring.
• Total synthesis of 15(RS)-5,6-dehydro-8-epi-PGF2α methyl ester by a biomimetic process
  作者：Alexandre Guy、Thierry Durand、Jean-Pierre Vidal、Jean-Claude Rossi

  DOI：10.1016/s0040-4039(97)00100-7

  日期：1997.3

  The first total synthesis of 15(RS)-5,6-dehydro-8-epi-PGF(2 alpha) methyl ester 1 with high stereoselectivity and good yield, is described using D-glucose as starting material. This novel isoprostane is a potent precursor of labelled (deutered and/or tritiated) 8-epi-PGF(2 alpha), an useful tool for biological studies. (C) 1997 Published by Elsevier Science Ltd.
• Synthesis of labelled oxylipins: leukotriene A4 and 8-epi-prostaglandin F2α
  作者：V. P. Shevchenko、I. Yu. Nagaev、N. F. Myasoedov、A. Guy、T. Durand、A. Vidal、J-P. Vidal、J-C. Rossi、V. V. Bezuglov

  DOI：10.1002/(sici)1099-1344(199907)42:7<663::aid-jlcr228>3.0.co;2-k

  日期：1999.7

  Tritiated leukotriene A(4) and 8-epi-prostaglandin F-2 alpha methyl esters were prepared from the corresponding acetylenic precursors by selective reduction with tritium gas to provide a probe for the metabolite identification of these oxylipins. Partially deactivated Pd-catalysts were prepared from commercial products and their composition was optimized to achieve the better selectivity. A micro-method for the saponification of labelled oxylipins methyl esters was used.