3-tert-butyldimethylsilyloxy-17α,20R-epoxy-20-hydroxymethyl-1,3,5(10),17(20)estratetraene | 206442-57-1

• 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: 3-tert-butyldimethylsilyloxy-17α,20R-epoxy-20-hydroxymethyl-1,3,5(10),17(20)estratetraene
• 英文别名: [(2'R,8R,9S,13S,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-13-methylspiro[7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17,3'-oxirane]-2'-yl]methanol
• CAS: 206442-57-1
• 化学式: C₂₆H₄₀O₃Si
• 分子量: 428.687
• InChiKey: GLCJPGGKAASWRN-YTUIUPOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-tert-butyldimethylsilyloxy-17α,20R-epoxy-20-hydroxymethyl-1,3,5(10),17(20)estratetraene 在 四氯化碳 、 正丁基锂 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.5h， 生成 19-去甲孕甾-1,3,5(10)-三烯-20-炔-3,17-二醇
  参考文献：
  名称：

  An efficient synthesis of 17-epi-ethynylestradiol

  摘要：

  An efficient synthesis has been developed yielding 17-epi-ethynylestradiol 2 in an overall yield of 17%. The key derivatives 7a-c were prepared from estrone in four steps. Subsequently epoxides 7a,c were efficiently transformed into 2 via Takano's method. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00124-0
• 作为产物：
  描述：

  2-[3-(tert-butyl-dimethyl-silanoxy)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrocyclopenta[a]phenanthren-17-ylidene]-ethanol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(2'S,8R,9S,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-13-methylspiro[7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17,3'-oxirane]-2'-yl]methanol 、 [(2'S,8R,9S,13S,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-13-methylspiro[7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17,3'-oxirane]-2'-yl]methanol 、 3-tert-butyldimethylsilyloxy-17α,20R-epoxy-20-hydroxymethyl-1,3,5(10),17(20)estratetraene
  参考文献：
  名称：

  An efficient synthesis of 17-epi-ethynylestradiol

  摘要：

  An efficient synthesis has been developed yielding 17-epi-ethynylestradiol 2 in an overall yield of 17%. The key derivatives 7a-c were prepared from estrone in four steps. Subsequently epoxides 7a,c were efficiently transformed into 2 via Takano's method. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00124-0

文献信息

• An efficient synthesis of 17-epi-ethynylestradiol
  作者：Christian L.J. Ewers、Michael Harre、Jörg Mohr、Klaus Nickisch、Ulf Tilstam

  DOI：10.1016/s0040-4020(98)00124-0

  日期：1998.4

  An efficient synthesis has been developed yielding 17-epi-ethynylestradiol 2 in an overall yield of 17%. The key derivatives 7a-c were prepared from estrone in four steps. Subsequently epoxides 7a,c were efficiently transformed into 2 via Takano's method. (C) 1998 Elsevier Science Ltd. All rights reserved.