(5Z,7E)-(1S,3R,23R)-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-23-(methylthiothiocarbonyloxy)-9,10-seco-5,7,10(19)-cholestatriene | 303015-24-9

• 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)-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-23-(methylthiothiocarbonyloxy)-9,10-seco-5,7,10(19)-cholestatriene
• CAS: 303015-24-9
• 化学式: C₄₃H₇₂F₆O₅S₂Si₂
• 分子量: 903.335
• InChiKey: BPNZZNFXTJAVRA-IIYWTWNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.12
• 重原子数：
  58.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (5Z,7E)-(1S,3R,23R)-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-23-(methylthiothiocarbonyloxy)-9,10-seco-5,7,10(19)-cholestatriene 在 甲烷磺酸 、 三正丁基氢锡 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.0h， 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：

  (4R)-4-((1R,3aS,7aR,E)-4-((Z)-2-((3S,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methylenecyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)pentan-2-ol 在 四丙基高钌酸铵 咪唑 、 氢氧化钾 、 sodium tetrahydroborate 、 N-甲基吲哚酮 、 4 Angstroem MS 、 sodium hydride 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 16.92h， 生成 (5Z,7E)-(1S,3R,23R)-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-23-(methylthiothiocarbonyloxy)-9,10-seco-5,7,10(19)-cholestatriene
  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