(5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10(19)-cholestatrien-25-ol | 303015-21-6

• 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,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10(19)-cholestatrien-25-ol
• CAS: 303015-21-6
• 化学式: C₄₁H₆₈F₆O₅Si₂
• 分子量: 811.149
• InChiKey: SOTQYILDRDGUAP-BBOYFXAGSA-N

物化性质

• 沸点：
  656.9±55.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.39
• 重原子数：
  54.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10(19)-cholestatrien-25-ol 在 咪唑 、 氢氧化钾 、 甲烷磺酸 、 三正丁基氢锡 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 甲苯 为溶剂， 反应 7.0h， 生成 氟骨三醇
  参考文献：
  名称：

  Synthesis and biological evaluations of A-ring isomers of 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D 3

  摘要：

  The activated vitamin D-3 derivative 26,27-F-6-1 alpha,25(OH)(2)D-3 (2a), its three A-ring diastereomers (2b, 2c, 2d), and 5,6-trans isomer (2e) were prepared. Two analogues (2b, 2c) of these isomers were synthesized by a palladium catalyzed coupling reaction using Vinyl bromide 5 and enynes (6a, 6b), which were derived from readily commercially available 2S-(+)-glycidyl p-toluenesulfonate 7, as a common starting material. Competitive vitamin D receptor (VDR) binding affinities of these diastereomers of 2a were evaluated. Interestingly, the stereochemical effects at C-1,3 of 2a were considerably more moderate than those of 1 alpha,25(OH)(2)D-3 (1). In particular, isomerization at the 5,6-double bond of 2a only slightly reduced VDR affinity, whereas 5,6-trans-1 alpha,25(OH)(2)D-3 had a significantly lower binding affinity than 1. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00142-5
• 作为产物：
  描述：

  1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(Z),7(E),10(19)-triene 在 sodium tetrahydroborate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 反应 12.67h， 生成 (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10(19)-cholestatrien-25-ol
  参考文献：
  名称：

  Synthesis and biological evaluations of A-ring isomers of 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D 3

  摘要：

  The activated vitamin D-3 derivative 26,27-F-6-1 alpha,25(OH)(2)D-3 (2a), its three A-ring diastereomers (2b, 2c, 2d), and 5,6-trans isomer (2e) were prepared. Two analogues (2b, 2c) of these isomers were synthesized by a palladium catalyzed coupling reaction using Vinyl bromide 5 and enynes (6a, 6b), which were derived from readily commercially available 2S-(+)-glycidyl p-toluenesulfonate 7, as a common starting material. Competitive vitamin D receptor (VDR) binding affinities of these diastereomers of 2a were evaluated. Interestingly, the stereochemical effects at C-1,3 of 2a were considerably more moderate than those of 1 alpha,25(OH)(2)D-3 (1). In particular, isomerization at the 5,6-double bond of 2a only slightly reduced VDR affinity, whereas 5,6-trans-1 alpha,25(OH)(2)D-3 had a significantly lower binding affinity than 1. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00142-5