15(RS)-5,6-dehydro-8-epi-PGF_2α methyl ester | 188255-10-9

• 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: 15(RS)-5,6-dehydro-8-epi-PGF_2α methyl ester
• 英文别名: methyl 7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-ynoate
• CAS: 188255-10-9
• 化学式: C₂₁H₃₄O₅
• 分子量: 366.498
• InChiKey: GYPGTUAFSDZKQM-LVSAOAGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  15(RS)-5,6-dehydro-8-epi-PGF_2α methyl ester 在 sodium tetrahydroborate 、 Pd-BaSO₄ 、 lead acetate sodium hydroxide 、 超重氢 、 三乙胺 作用下， 以 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 4.5h， 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：

  (8S,9S,11R)-methyl 9,11-dihydroxy-8-iodoeicosa-12E,14-dien-5-ynoate 在 air 、 三乙基硼 、 三正丁基氢锡 、 三苯基膦 作用下， 以 对二甲苯 为溶剂， 反应 2.33h， 以33%的产率得到15(RS)-5,6-dehydro-8-epi-PGF_2α methyl ester
  参考文献：
  名称：

  Total Synthesis of (15R)- and (15S)-F_2t-Isoprostanes by a Biomimetic Process Using the Cyclization of Acyclic Dihydroxylated Octa-5,7-dienyl Radicals

  摘要：

  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.

  DOI：

  10.1021/jo0109624

文献信息

• 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.