3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(Z),7(E),10(19)-triene SO2 adduct | 344798-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: 3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(Z),7(E),10(19)-triene SO2 adduct
• 英文别名: (2S)-2-[(1R,3aS,4E,7aR)-4-[[(6S)-6-[tert-butyl(dimethyl)silyl]oxy-2,2-dioxo-1,3,4,5,6,7-hexahydro-2-benzothiophen-1-yl]methylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propan-1-ol
• CAS: 344798-31-8
• 化学式: C₂₈H₄₈O₄SSi
• 分子量: 508.838
• InChiKey: VGPRIHGJOIJOMO-SGNOMLJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(Z),7(E),10(19)-triene SO2 adduct 在 咪唑 、 碘 、 碳酸氢钠 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene
  参考文献：
  名称：

  Nickel-Mediated Conjugate Addition. Elaboration of Calcitriol from Ergocalciferol

  摘要：

  DOI：

  10.1021/jo00125a051
• 作为产物：
  描述：

  维他命D2二氧化硫加合物 在 咪唑 、 sodium tetrahydroborate 、 sodium acetate 、 臭氧 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(Z),7(E),10(19)-triene SO2 adduct
  参考文献：
  名称：

  A Stereospecific Synthesis of 24(S)-Hydroxyvitamin D₂, a Prodrug for 1α,24(S)-Dihydroxyvitamin D₂

  摘要：

  This contribution describes the first stereospecific synthesis of 24(S)-hydroxyvitamin D-2 (1), a metabolite of vitamin D-2. This metabolite acts as a prodrug for 1alpha,24 (S)-dihydroxy vitamin D-2 (2). which is under development for treatment of various diseases characterized by cellular hyperproliferation. The key step of the synthesis involves the Wittig-Horner olefination of (S)-2,3-dimethyl-2-triethysilyloxybutyraldehyde (17) and a vitamin D2 phosphine oxide derivative (22). The synthesis of the requisite aldehyde started with the commercially available L-(+)-valine and was completed in seven steps. The vitamin D-2 phosphine oxide derivative was synthesized in seven steps starting from vitamin D-2.

  DOI：

  10.1021/op010229e

文献信息

• An Improved Synthesis of 24,24-Difluoro-1.ALPHA.,25-dihydroxyvitamin D3 from Readily Available Vitamin D2.
  作者：Kaori ANDO、Fumiaki KOIKE、Fumihiro KONDO、Hiroaki TAKAYAMA

  DOI：10.1248/cpb.43.189

  日期：——

  An improved synthesis of a highly potent vitamin D3 analog, 24, 24-difluoro-1α, 25-dihydroxyvitamin D3 (1b)has been accomplished via vitamin D2-SO2 adducts. The introduction of fluorine atoms was performed by treating the α-keto ester (11) with diethylaminosulfur trifluoride. The total yield was 12.5% from inexpensive vitamin D2 in 11 steps. This sequence is sufficiently straightforward to be conducted on a gram scale.

  通过维生素D2-SO2加合物，完成了一种高效能维生素D3类似物24, 24-二氟-1α, 25-二羟基维生素D3 (1b) 的改进合成。引入氟原子的过程是通过用二乙胺硫三氟化物处理α-酮酯（11）来实现的。该方法从廉价的维生素D2中在11个步骤中获得了12.5%的总产率。这一序列简单明了，足以在克级规模上进行。
• Affinity-based protein profiling identifies vitamin D3 as a heat shock protein 70 antagonist that regulates hedgehog transduction in murine basal cell carcinoma
  作者：Jiachen Wen、M. Kyle Hadden

  DOI：10.1016/j.ejmech.2021.114005

  日期：2022.1

  Vitamin D3 (VD3) is a seco-steroid that inhibits the Hedgehog (Hh) signaling pathway. Initial studies suggested its anti-Hh activity results from direct inhibition of Smoothened, a seven-transmembrane cell surface receptor that is a key regulator of the Hh signaling cascade. More recently, a role for the Vitamin D Receptor in mediating inhibition of Hh-signaling by seco-steroid has been suggested.

  维生素 D3 (VD3) 是一种抑制 Hedgehog (Hh) 信号通路的seco类固醇。初步研究表明，它的抗 Hh 活性是直接抑制 Smoothened 的结果，Smoothened 是一种七跨膜细胞表面受体，是 Hh 信号级联的关键调节剂。最近，已经提出维生素 D 受体在介导seco类固醇抑制 Hh 信号传导中的作用。在此，进行了一项基于亲和力的蛋白质分析研究，以更好地了解控制 VD3 介导的抗 Hh 活性的细胞蛋白质。我们合成了一种新的生物素化 VD3 类似物 ( 8 ) 用作化学探针来探索seco的细胞结合目标。-甾体支架。通过一系列下拉实验和后续质谱分析，确定热休克蛋白 70 (Hsp70) 是 VD3 的主要结合蛋白。通过一系列生化和细胞测定，Hsp70 被证实为 VD3 的结合靶标。VD3 与 Hsp70 具有微摩尔亲和力。此外，Hsp70 表达的选择性敲低和已知 Hsp70
• A Stereospecific Synthesis of 24(<i>S</i>)-Hydroxyvitamin D₂, a Prodrug for 1α,24(<i>S</i>)-Dihydroxyvitamin D₂
  作者：Lisa D. Coutts、William B. Geiss、Brian T. Gregg、Mark A. Helle、Chi-Hsin R. King、Zinovy Itov、Mary E. Mateo、Harold Meckler、Mark W. Zettler、Joyce C. Knutson

  DOI：10.1021/op010229e

  日期：2002.5.1

  This contribution describes the first stereospecific synthesis of 24(S)-hydroxyvitamin D-2 (1), a metabolite of vitamin D-2. This metabolite acts as a prodrug for 1alpha,24 (S)-dihydroxy vitamin D-2 (2). which is under development for treatment of various diseases characterized by cellular hyperproliferation. The key step of the synthesis involves the Wittig-Horner olefination of (S)-2,3-dimethyl-2-triethysilyloxybutyraldehyde (17) and a vitamin D2 phosphine oxide derivative (22). The synthesis of the requisite aldehyde started with the commercially available L-(+)-valine and was completed in seven steps. The vitamin D-2 phosphine oxide derivative was synthesized in seven steps starting from vitamin D-2.
• Nickel-Mediated Conjugate Addition. Elaboration of Calcitriol from Ergocalciferol
  作者：Percy S. Manchand、George P. Yiannikouros、Peter S. Belica、Pradeep Madan

  DOI：10.1021/jo00125a051

  日期：1995.10