(5Z,7E)-(1S,3R,20R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18,20-epoxy-25-[(methoxymethyl)oxy]-21-nor-9,10-secocholesta-5,7,10(19)-triene | 442200-84-2

• 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: (5Z,7E)-(1S,3R,20R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18,20-epoxy-25-[(methoxymethyl)oxy]-21-nor-9,10-secocholesta-5,7,10(19)-triene
• 英文别名: [(1S,3Z,5R)-3-[(2E)-2-[(3R,3aS,5aS,9aR)-3-[4-(methoxymethoxy)-4-methylpentyl]-3,3a,4,5,5a,7,8,9-octahydro-1H-indeno[1,7a-c]furan-6-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylidenecyclohexyl]oxy-tert-butyl-dimethylsilane
• CAS: 442200-84-2
• 化学式: C₄₀H₇₂O₅Si₂
• 分子量: 689.18
• InChiKey: ODZVUYWIXOWZIW-JPORZWECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.13
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5Z,7E)-(1S,3R,20R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18,20-epoxy-25-[(methoxymethyl)oxy]-21-nor-9,10-secocholesta-5,7,10(19)-triene 在 四丁基氟化铵 、 AG 50W-X₄ resin 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 44.0h， 以75%的产率得到(5Z,7E)-(1S,3R,20R)-18,20-epoxy-21-nor-9,10-secocholesta-5,7,10(19)-trien-1,3,25-triol
  参考文献：
  名称：

  Synthesis of New 18-Substituted Analogues of Calcitriol Using a Photochemical Remote Functionalization

  摘要：

  A novel convergent synthetic approach to new analogues of calcitriol modified at the C-18 position is reported. The key step in the synthesis is the 20-hydroxyl-directed photochemical iodination of the 18-methyl group in the presence of (diacetoxyiodo)benzene. Using this methodology, two new analogues of calcitriol were prepared: the first contains a hydroxylated alkyl side chain attached at C-18 with the natural side chain replaced by an isopropylidene group; the second is a conformationally locked analogue due to an extra oxacycle between the C-18 and C-20 positions.

  DOI：

  10.1021/jo020022z
• 作为产物：
  描述：

  (8β)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18-iodopregnan-20-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 重铬酸吡啶 、 正丁基锂 、 mercury(II) diacetate 、 四丁基氟化铵 、 silver(I) acetate 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 211.5h， 生成 (5Z,7E)-(1S,3R,20R)-1,3-di[(tert-butyldimethylsilyl)oxy]-18,20-epoxy-25-[(methoxymethyl)oxy]-21-nor-9,10-secocholesta-5,7,10(19)-triene
  参考文献：
  名称：

  Synthesis of New 18-Substituted Analogues of Calcitriol Using a Photochemical Remote Functionalization

  摘要：

  A novel convergent synthetic approach to new analogues of calcitriol modified at the C-18 position is reported. The key step in the synthesis is the 20-hydroxyl-directed photochemical iodination of the 18-methyl group in the presence of (diacetoxyiodo)benzene. Using this methodology, two new analogues of calcitriol were prepared: the first contains a hydroxylated alkyl side chain attached at C-18 with the natural side chain replaced by an isopropylidene group; the second is a conformationally locked analogue due to an extra oxacycle between the C-18 and C-20 positions.

  DOI：

  10.1021/jo020022z