17-{[(trifluoromethyl)sulfonyl]oxy}-18a-homoestra-5,16-diene-3,11-dione cyclic 3-(1,2-ethanediyl acetal) | 191029-90-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 17-{[(trifluoromethyl)sulfonyl]oxy}-18a-homoestra-5,16-diene-3,11-dione cyclic 3-(1,2-ethanediyl acetal)
• 英文别名: [(8S,9S,10R,13S,14S)-13-ethyl-11-oxospiro[1,2,4,7,8,9,10,12,14,15-decahydrocyclopenta[a]phenanthrene-3,2'-1,3-dioxolane]-17-yl] trifluoromethanesulfonate
• CAS: 191029-90-0
• 化学式: C₂₂H₂₇F₃O₆S
• 分子量: 476.514
• InChiKey: IZQKNQUEGIRYPS-DAELLWKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  17-{[(trifluoromethyl)sulfonyl]oxy}-18a-homoestra-5,16-diene-3,11-dione cyclic 3-(1,2-ethanediyl acetal) 在 四(三苯基膦)钯 吡啶 、 chromium(VI) oxide 、 sodium tetrahydroborate 、 2,6-二叔丁基吡啶 、 氨 、 lithium 、 sodium carbonate 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 17β-(4-methoxyphenyl)-11-{[(trifluoromethyl)sulfonyl]oxy}-18a-homoestra-5,9(11)-dien-3-one cyclic (1,2-ethanediyl acetal)
  参考文献：
  名称：

  Highly diastereoselective synthesis of 11β,17β-diaryl-18a-homo-19-nor steroids

  摘要：

  In a highly diastereoselective fashion novel 11 beta, 17 beta-diaryl steroids 17 and 18 were synthesized via Birch-type reduction [1] of styrylic precursors 11 and 15. Both precursors were readily available by Suzuki-type coupling reactions [2] of aromatic boronic acids [3] and the corresponding enol triflates 6, 10, and 14. Regioselective 17-enol triflate formation in presence of a 11-keto function could be demonstrated in case of steroid 5. The remarkably high degree of stereoselectivity observed parallels results from the natural series [4] and demonstrated a broader applicability of such single electron transfer reductions in stereoselective transformations on the steroid skeleton.

  DOI：

  10.1002/prac.19973390164
• 作为产物：
  描述：

  三氟甲磺酸酐 、 18a-methylestr-5-ene-3,11,17-trione cyclic 3-(1,2-ethanediyl acetal) 在 2,6-二叔丁基吡啶 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到17-{[(trifluoromethyl)sulfonyl]oxy}-18a-homoestra-5,16-diene-3,11-dione cyclic 3-(1,2-ethanediyl acetal)
  参考文献：
  名称：

  Highly diastereoselective synthesis of 11β,17β-diaryl-18a-homo-19-nor steroids

  摘要：

  In a highly diastereoselective fashion novel 11 beta, 17 beta-diaryl steroids 17 and 18 were synthesized via Birch-type reduction [1] of styrylic precursors 11 and 15. Both precursors were readily available by Suzuki-type coupling reactions [2] of aromatic boronic acids [3] and the corresponding enol triflates 6, 10, and 14. Regioselective 17-enol triflate formation in presence of a 11-keto function could be demonstrated in case of steroid 5. The remarkably high degree of stereoselectivity observed parallels results from the natural series [4] and demonstrated a broader applicability of such single electron transfer reductions in stereoselective transformations on the steroid skeleton.

  DOI：

  10.1002/prac.19973390164

文献信息

• Highly diastereoselective synthesis of 11β,17β-diaryl-18a-homo-19-nor steroids
  作者：Eckhard Ottow、Arwed Cleve、Günter Neef、Wolfgang Schwede

  DOI：10.1002/prac.19973390164

  日期：——

  In a highly diastereoselective fashion novel 11 beta, 17 beta-diaryl steroids 17 and 18 were synthesized via Birch-type reduction [1] of styrylic precursors 11 and 15. Both precursors were readily available by Suzuki-type coupling reactions [2] of aromatic boronic acids [3] and the corresponding enol triflates 6, 10, and 14. Regioselective 17-enol triflate formation in presence of a 11-keto function could be demonstrated in case of steroid 5. The remarkably high degree of stereoselectivity observed parallels results from the natural series [4] and demonstrated a broader applicability of such single electron transfer reductions in stereoselective transformations on the steroid skeleton.