(20S)-des-A,B-20-[4'-(tert-butyldimethylsilyloxy)-4'-methylpent-(1'E)-en-yl]-pregnan-8-one | 1283571-21-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (20S)-des-A,B-20-[4'-(tert-butyldimethylsilyloxy)-4'-methylpent-(1'E)-en-yl]-pregnan-8-one
• 英文别名: (1R,3aR,7aR)-1-[(E,2S)-6-[tert-butyl(dimethyl)silyl]oxy-6-methylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-one
• CAS: 1283571-21-0
• 化学式: C₂₄H₄₄O₂Si
• 分子量: 392.698
• InChiKey: PWSOXDLFCLJUQB-ZGUBBUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.15
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (20S)-des-A,B-20-[4'-(tert-butyldimethylsilyloxy)-4'-methylpent-(1'E)-en-yl]-pregnan-8-one 在 氢氟酸 、 苯基锂 作用下， 以 四氢呋喃 、 二丁醚 、 水 、 乙腈 为溶剂， 反应 32.5h， 生成 (20S,22E)-2-methylene-19-nor-22-ene-1α,25-dihydroxyvitamin D₃
  参考文献：
  名称：

  [EN] (20S,22E)-2-METHYLENE-19-NOR-22-ENE-1a,25-DIHYDROXYVITAMIN D3 ANALOGS
  [FR] (20S,22E)-2-MÉTHYLÈNE-19-NOR-22-ÈNE-1a,25-DIHYDROXYVITAMINE D3

  摘要：

  公开号：

  WO2011041579A3
• 作为产物：
  描述：

  (20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al 在 2,6-二甲基吡啶 、 正丁基锂 、 四丙基高钌酸铵 、 乙醇 、 N-甲基吗啉氧化物 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 47.0h， 生成 (20S)-des-A,B-20-[4'-(tert-butyldimethylsilyloxy)-4'-methylpent-(1'E)-en-yl]-pregnan-8-one
  参考文献：
  名称：

  [EN] (20S,22E)-2-METHYLENE-19-NOR-22-ENE-1a,25-DIHYDROXYVITAMIN D3 ANALOGS
  [FR] (20S,22E)-2-MÉTHYLÈNE-19-NOR-22-ÈNE-1a,25-DIHYDROXYVITAMINE D3

  摘要：

  公开号：

  WO2011041579A3

文献信息

• 26-Desmethyl-2-methylene-22-ene-19-nor-1α,25-dihydroxyvitamin D3 compounds selectively active on intestine
  作者：Grazia Chiellini、Pawel Grzywacz、Lori A. Plum、Margaret Clagett-Dame、Hector F. DeLuca

  DOI：10.1016/j.steroids.2014.01.012

  日期：2014.5

  Six new analogs of 2-methylene-19-nor-1 alpha,25-dihydroxyvitamin D-3, 6-7 and 8a,b-9a,b, have been synthesized. All compounds are characterized by a trans double bond located in the side chain between C-22 and C-23. While compounds 6 and 7 possess C-26 and C-27 methyls, compounds 8a,b and 9a,b lack one of these groups. A Lythgoe-based synthesis, employing the Wittig-Horner reaction was used for these preparations. Two different types of Delta E-22-25-hydroxy Grundmann's ketone, having either only one stereogenic center located at position C-20 (20 and 21), or two stereogenic centers located at 20- and 25-positions (24a,b-25a,b) were obtained by a multi-step procedure from commercial vitamin D-2. The introduction of a double bond at C-22 appeared to lower biological activity in vitro and in vivo. Further removal of a 26-methyl in these analogs had little effect on receptor binding, HL-60 differentiation and CYP24A expression but markedly diminished or eliminated in vivo activity on bone calcium mobilization while retaining activity on intestinal calcium transport. (C) 2014 Elsevier Inc. All rights reserved.
• [EN] (20S,22E)-2-METHYLENE-19-NOR-22-ENE-1a,25-DIHYDROXYVITAMIN D3 ANALOGS<br/>[FR] (20S,22E)-2-MÉTHYLÈNE-19-NOR-22-ÈNE-1a,25-DIHYDROXYVITAMINE D3
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2011041579A3

  公开（公告）日：2011-06-03