(3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane | 387834-42-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: (3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
• 英文别名: tert-butyl-[(1R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylidene]cyclohexyl]oxy-dimethylsilane
• CAS: 387834-42-6
• 化学式: C₂₅H₅₁BO₄Si₂
• 分子量: 482.66
• InChiKey: UWRVEINNASFGSW-NHCUHLMSSA-N

物化性质

• 沸点：
  441.7±55.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 氢氧化钾 、 氢氟酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (1S,3S)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-羟基-6-甲基庚烷-2-基]-7a-甲基-2,3,3a,5,6,7-六氢-1H-茚-4-亚基]亚乙基]环己烷-1,3-二醇
  参考文献：
  名称：

  Novel Synthetic Approach to 19-nor-1α,25-Dihydroxyvitamin D₃ and Its Derivatives by Suzuki−Miyaura Coupling in Solution and on Solid Support

  摘要：

  [GRAPHICS]19-nor-1 alpha ,25-Dihydroxyvitamin D-3 was synthesized by the Suzuki-Miyaura coupling of the A-ring intermediate 3, which was efficiently prepared from readily available 5-(tert butyldimethylsilyl)oxycyclohex-2-enone (5), with the boronate compound of the C,D-ring portion. The method could be applied to a solid-phase synthesis to prepare the des-C,D derivatives of 19-nor-1 alpha ,25-dihydroxyvitamin D-3.

  DOI：

  10.1021/ol016908r
• 作为产物：
  描述：

  (1R,5R)-(Z)-3-bromomethylene-5-(tert-butyldimethyl-silanyloxy)cyclohexanol 在 咪唑 、 叔丁基锂 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 37.0h， 生成 (3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
  参考文献：
  名称：

  Novel Synthetic Approach to 19-nor-1α,25-Dihydroxyvitamin D₃ and Its Derivatives by Suzuki−Miyaura Coupling in Solution and on Solid Support

  摘要：

  [GRAPHICS]19-nor-1 alpha ,25-Dihydroxyvitamin D-3 was synthesized by the Suzuki-Miyaura coupling of the A-ring intermediate 3, which was efficiently prepared from readily available 5-(tert butyldimethylsilyl)oxycyclohex-2-enone (5), with the boronate compound of the C,D-ring portion. The method could be applied to a solid-phase synthesis to prepare the des-C,D derivatives of 19-nor-1 alpha ,25-dihydroxyvitamin D-3.

  DOI：

  10.1021/ol016908r

文献信息

• Synthesis and vitamin D receptor affinity of 16-oxa vitamin D₃ analogues
  作者：Kouta Ibe、Takeshi Yamada、Sentaro Okamoto

  DOI：10.1039/c9ob02339a

  日期：——

  Two novel 16-oxa-vitamin D3 analogues were synthesized using a tandem Ti(II)-mediated enyne cyclization/Cu-catalyzed allylation, Ru-catalyzed ring-closing metathesis reaction, and a low-valent titanium (LVT)-mediated stereoselective radical reduction of 8α,14α-epoxide as the key steps for the synthesis of the 16-oxa-C,D ring unit. The vitamin D receptor-binding affinity of the synthesized analogues

  使用串联的Ti（II）介导的烯炔环化/ Cu催化的烯丙基化，Ru催化的闭环复分解反应和低价钛（LVT）介导的立体选择性合成了两个新颖的16-氧杂-维生素D 3类似物自由基还原8α，14α-环氧化物是合成16-oxa-C，D环单元的关键步骤。通过荧光评估合成的类似物16-oxa-1α，25-（OH）2 VD 3和16-oxa-19-或-1α，25-（OH）2 VD 3的维生素D受体结合亲和力。极化维生素D受体竞争剂测定法和时间分辨荧光能量转移维生素D受体共激活剂测定法。
• Design, synthesis, and properties of des-D-ring interphenylene derivatives of 1α,25-Dihydroxyvitamin D3
  作者：Kouta Ibe、Haruki Nakada、Mayu Ohgami、Takeshi Yamada、Sentaro Okamoto

  DOI：10.1016/j.ejmech.2022.114795

  日期：2022.12

  (NR1I1) reporter assay revealed that the des-D-ring interphenylene analogs exhibited a certain VDR binding affinity and ability to promote gene transcription. In particular, analogs having a side chain with an appropriate length at meta position showed high gene transcription promoting activities comparable to those of 1α,25-dihydroxyvitamin D3 and its 19-nor derivative.

  维生素 D 3的新型去-D-环间亚苯基类似物是基于它们的构象分析和使用配体-蛋白质对接模拟估计的对维生素 D 受体 (VDR) 的亲和力而设计的。根据该设计，通过des-D、C-环和A-环中间体的Suzuki-Miyaura偶联反应合成了一系列des - D-环间亚苯基类似物。荧光偏振 VDR 竞争者测定、时间分辨荧光共振能量转移 VDR 共激活剂结合测定和人类 VDR (NR1I1) 报告基因测定表明，des-D-环间亚苯基类似物表现出一定的VDR结合亲和力和促进基因转录的能力。特别地，在间位具有适当长度的侧链的类似物显示出与1α，25-二羟基维生素D 3及其19 - nor衍生物相当的高基因转录促进活性。
• Novel Synthetic Approach to 19-<i>nor</i>-1α,25-Dihydroxyvitamin D₃ and Its Derivatives by Suzuki−Miyaura Coupling in Solution and on Solid Support
  作者：Takeshi Hanazawa、Takeshi Wada、Tomoko Masuda、Sentaro Okamoto、Fumie Sato

  DOI：10.1021/ol016908r

  日期：2001.11.1

  [GRAPHICS]19-nor-1 alpha ,25-Dihydroxyvitamin D-3 was synthesized by the Suzuki-Miyaura coupling of the A-ring intermediate 3, which was efficiently prepared from readily available 5-(tert butyldimethylsilyl)oxycyclohex-2-enone (5), with the boronate compound of the C,D-ring portion. The method could be applied to a solid-phase synthesis to prepare the des-C,D derivatives of 19-nor-1 alpha ,25-dihydroxyvitamin D-3.