des-A,B-25-(ethoxymethyloxy)cholestan-8-one | 1190696-99-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: des-A,B-25-(ethoxymethyloxy)cholestan-8-one
• 英文别名: (1R,3aR,7aR)-1-[(2R)-6-(ethoxymethoxy)-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-one
• CAS: 1190696-99-1
• 化学式: C₂₁H₃₈O₃
• 分子量: 338.531
• InChiKey: CNCFJWXMCSIXCR-DCXXXQMHSA-N

物化性质

• 沸点：
  407.5±15.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  des-A,B-25-(ethoxymethyloxy)cholestan-8-one 在 咪唑 、 正丁基锂 、 (-)-CSA 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (R)-6-{(1R,3aS,7aR)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol
  参考文献：
  名称：

  维生素D 3类似物偶联的ORMOSIL纳米颗粒的制备及其生物学评价†

  摘要：

  通过乙烯基三乙氧基硅烷在表面活性剂稳定的微乳液中缩合并与几种维生素D 3衍生物缀合，制备了染料掺杂的直径90 nm的多功能有机改性二氧化硅（ORMOSIL）纳米颗粒。为此，已经合成了具有至少一个衍生为碳酸乙烯基酯的羟基的维生素D类似物。这些类似物通过碳酸盐官能团结合到ORMOSIL纳米颗粒上，形成维生素D纳米颗粒的氨基甲酸酯衍生物。通过表面等离振子共振研究了这些纳米颗粒与作为不可溶维生素D 3的血清转运蛋白之一的人血清白蛋白之间的相互作用。获得的结果表明，这种方法可以获取水溶性维生素D3种衍生物，可保持其完整的蛋白质结合能力。

  DOI：

  10.1039/c6ra02965e
• 作为产物：
  描述：

  艾地骨化醇中间体 在 4-二甲氨基吡啶 、 ruthenium trichloride 、 sodium periodate 、 potassium dihydrogenphosphate 、 N,N-二异丙基乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 乙腈 为溶剂， 生成 des-A,B-25-(ethoxymethyloxy)cholestan-8-one
  参考文献：
  名称：

  Synthesis of vitamin D3 analogues with A-ring modifications to directly measure vitamin D levels in biological samples

  摘要：

  C-3-substituted 25-hydroxyvitamin D-3 analogues were synthesized as tools to directly measure levels of vitamin D in biological samples. The strategy involves vinyloxycarbonylation of the 3 beta-hydroxy group and formation of a carbamate bond with a hydroxyl or amino group at the end of the alkyl chain. Biotinylated conjugates of synthesized derivatives were generated to be linked with vitamin D binding protein (DBP). The spacer group present in the alkyl chain is important in the binding of antibodies to the analogue-DBP complex. When compared to 25-hydroxyvitamin D-3-DBP, the binding of some antibodies to the analogue-DBP complex of the 25-hydroxyvitamin D-3 derivative 10 that posses an 8-aminoctyl alkyl chain is significantly reduced, but this analogue displaced [26,27-H-3]-25-hydroxyvitamin D-3 from DBP. In contrast, the 8-hydroxyoctyl alkyl chain analogue 9 showed less displacement. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.013

文献信息

• Synthesis, Conformational Analysis, and Biological Evaluation of 19-<i>nor</i>-Vitamin D₃ Analogues with A-Ring Modifications
  作者：Laura Sánchez-Abella、Susana Fernández、Annemieke Verstuyf、Lieve Verlinden、Vicente Gotor、Miguel Ferrero

  DOI：10.1021/jm900711d

  日期：2009.10.8

  We have synthesized several isomers of 19-nor-vitamin D analogues possessing a hydroxy group at C-2 as well as novel derivatives bearing an epoxy substituent at the A-ring. All vitamins were prepared in convergent syntheses utilizing the modified Julia olefination. 1α,2α,25-Trihydroxy-19-nor-vitamin D3 (3) and 2β,3β-epoxy-1α,25-dihydroxy-3-deoxy-19-nor-vitamin D3 (10), which showed the highest affinity

  我们已经合成了在C-2处具有羟基的19-或-维生素D类似物的几种异构体，以及在A环上带有环氧取代基的新型衍生物。所有的维生素都是利用聚变的朱莉娅烯化反应以收敛合成的方式制备的。1α，2α，25-三羟基-19-或-维生素D 3（3）和2β，3β-环氧-1α，25-二羟基-3-脱氧-19-或-维生素D 3（10），显示最高对维生素D受体的亲和力，在测试的化合物中表现出最高的抑制MCF-7乳腺癌细胞增殖的潜能。
• Synthesis of vitamin D3 analogues with A-ring modifications to directly measure vitamin D levels in biological samples
  作者：Alba Hernández-Martín、Tania González-García、Margaret Lawlor、Lesley Preston、Vicente Gotor、Susana Fernández、Miguel Ferrero

  DOI：10.1016/j.bmc.2013.10.013

  日期：2013.12

  C-3-substituted 25-hydroxyvitamin D-3 analogues were synthesized as tools to directly measure levels of vitamin D in biological samples. The strategy involves vinyloxycarbonylation of the 3 beta-hydroxy group and formation of a carbamate bond with a hydroxyl or amino group at the end of the alkyl chain. Biotinylated conjugates of synthesized derivatives were generated to be linked with vitamin D binding protein (DBP). The spacer group present in the alkyl chain is important in the binding of antibodies to the analogue-DBP complex. When compared to 25-hydroxyvitamin D-3-DBP, the binding of some antibodies to the analogue-DBP complex of the 25-hydroxyvitamin D-3 derivative 10 that posses an 8-aminoctyl alkyl chain is significantly reduced, but this analogue displaced [26,27-H-3]-25-hydroxyvitamin D-3 from DBP. In contrast, the 8-hydroxyoctyl alkyl chain analogue 9 showed less displacement. (C) 2013 Elsevier Ltd. All rights reserved.
• Preparation of ORMOSIL nanoparticles conjugated with vitamin D₃analogues and their biological evaluation
  作者：Tania González-García、Susana Fernández、Elisa Lubian、Fabrizio Mancin、Miguel Ferrero

  DOI：10.1039/c6ra02965e

  日期：——

  several vitamin D3 derivatives. For this, vitamin D analogues possessing at least one hydroxyl group derivatized as vinylcarbonate have been synthesized. These analogues were conjugated to ORMOSIL nanoparticles through the carbonate function, forming carbamate derivatives of vitamin D nanoparticles. The interaction between these nanoparticles and human serum albumin, which is one of the serum transporters

  通过乙烯基三乙氧基硅烷在表面活性剂稳定的微乳液中缩合并与几种维生素D 3衍生物缀合，制备了染料掺杂的直径90 nm的多功能有机改性二氧化硅（ORMOSIL）纳米颗粒。为此，已经合成了具有至少一个衍生为碳酸乙烯基酯的羟基的维生素D类似物。这些类似物通过碳酸盐官能团结合到ORMOSIL纳米颗粒上，形成维生素D纳米颗粒的氨基甲酸酯衍生物。通过表面等离振子共振研究了这些纳米颗粒与作为不可溶维生素D 3的血清转运蛋白之一的人血清白蛋白之间的相互作用。获得的结果表明，这种方法可以获取水溶性维生素D3种衍生物，可保持其完整的蛋白质结合能力。