(6Z)-(3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-3,25-diol-1-one | 210907-37-2

• 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: (6Z)-(3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-3,25-diol-1-one
• CAS: 210907-37-2
• 化学式: C₂₇H₃₆F₆O₃
• 分子量: 522.571
• InChiKey: KMUVTIXDCPEJKH-HPCORKKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.0
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (6Z)-(3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-3,25-diol-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以66%的产率得到(6Z)-(1R,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-1β,3β,25-triol
  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：

  氟骨三醇 在 戴斯-马丁氧化剂 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以66%的产率得到(6Z)-(3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-3,25-diol-1-one
  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