胆固醇叔丁基醚 | 1179-15-3

• 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
• 中文名称: 胆固醇叔丁基醚
• 英文名称: cholesteryl tert-butyl ether
• 英文别名: cholesteryl t-butyl ether；t-butyl cholesteryl ether；Cholesteryl-t-butylether；(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-3-[(2-methylpropan-2-yl)oxy]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene
• CAS: 1179-15-3
• 化学式: C₃₁H₅₄O
• 分子量: 442.769
• InChiKey: MTKZZYFLXGZJSQ-GTPODGLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  胆固醇叔丁基醚 、 双丙酮半乳糖 在 tetrabutylammonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 以16%的产率得到3β-O-(1',2':3',4'-di-O-isopropylidene-α-D-galactopyranos-6'-yl)cholest-5-ene
  参考文献：
  名称：

  Electrochemical synthesis of glycoconjugates from activated sterol derivatives

  摘要：

  Several derivatives of cholesterol and other 3 beta-hydroxy-Delta(5)-steroids were prepared and tested as sterol donors in electrochemical reactions with sugar alcohols. The reactions afforded glycoconjugates with sugar linked to a steroid moiety by an ether bond. Readily available sterol diphenylphosphates yielding up to 54% of the desired glycoconjugate were found to be the best sterol donors. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.01.007
• 作为产物：
  描述：

  胆固醇 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 胆固醇叔丁基醚
  参考文献：
  名称：

  菌株促进的不同化学类固醇化作用揭示了有效的抗炎伪类固醇糖苷

  摘要：

  开发具有免疫调节作用的新型药物是对抗炎症风暴对全球健康日益增长的威胁的有效方法。为了合成具有良好免疫调节潜力的醚键连接的假甾体糖苷，我们开发了一种新型甾体供体的高效脱氧功能化（甾体化），通过菌株释放促进，利用经济高效且易于获得的 Sc(OTf) 3催化。该转化产生瞬时类固醇-3-基碳阳离子，其容易与O- 、 C- 、 N- 、 S-和P-亲核试剂反应，生成结构多样的类固醇衍生物。进行 DFT 计算是为了揭示区域选择性的机制细节，这是受体依赖性类固醇模式的基础。这种方法可以很容易地扩展到糖醇的醚化，从而实现假类固醇糖苷的多样性导向、管道式合成，并具有良好至优异的产率，并具有用于抗炎剂发现的完整立体和区域特异性控制。免疫学研究表明，精心设计的胆固醇二糖可以显着抑制巨噬细胞中白细胞介素6的分泌，与阴性对照相比，抑制率高达99%。这些发现证实了假甾体糖苷作为开发新型抗炎药物的前瞻性先导药物的潜力。

  DOI：

  10.1021/jacs.4c00537

文献信息

• Unusual and Unexpected Reactivity of <i>t-</i>Butyl Dicarbonate (Boc₂O) with Alcohols in the Presence of Magnesium Perchlorate. A New and General Route to <i>t-</i>Butyl Ethers
  作者：Giuseppe Bartoli、Marcella Bosco、Manuela Locatelli、Enrico Marcantoni、Paolo Melchiorre、Letizia Sambri

  DOI：10.1021/ol047704o

  日期：2005.2.1

  [reaction: see text] A new mild method for protecting alcohols as t-butyl ethers is reported. The reaction proceeds with Mg(ClO4)2 and Boc2O and shows general applicability. The deprotection of t-butyl ethers has also been revisited. Preliminary results indicate the CeCl3 x 7H2O/NaI system is a very suitable catalyst for their removal.

  [反应：见正文]据报道，一种新的温和的保护叔丁醚醇的方法。反应与Mg（ClO4）2和Boc2O进行，显示出一般的适用性。也已经重新考虑了叔丁基醚的脱保护。初步结果表明，CeCl3 x 7H2O / NaI体系是非常适合去除它们的催化剂。
• Studies of organophosphorochloridates. Part II. Reactions of steroid phosphorodichloridates
  作者：R. J. W. Cremlyn、N. A. Olsson

  DOI：10.1039/j39710002023

  日期：——

  The preparation of the following steroid phosphorodichloridates is described: cholestanyl, epicholestanyl, epicholesteryl, and the derivatives of methyl 3α-hydroxy-5β-chlolanate, and ergosta-8(14)en-3β-ol. The formation of the phosphorodichloridates was followed by t.l.c. Attempted phosphorylation of 3,5-cyclocholestan-6β-ol, and 6β-hydroxycholest-4-en-3-ol gave cholesteryl phosphorodichloridate and

  描述了以下甾族二氯磷酸酯的制备：胆甾烷基，表胆固醇基，表胆固醇基以及3α-羟基-5β-氯戊酸甲酯的衍生物和ergosta-8（14）en-3β-ol。形成二氯二氯磷酸酯后，进行薄层色谱（tlc）。尝试将3,5-环胆甾烷-6β-ol和6β-羟基胆甾醇4-en-3-ol磷酸化，分别得到胆甾醇基二氯磷酸酯和胆甾烷3,6-二酮。已经在各种条件下检查了胆固醇二磷酸二氯酯的水解。类固醇二氯化磷已用甲醇处理。胆磷酸二氯胆固醇酯与多种醇的反应，得到相应的胆甾醇醚。用干燥的吡啶溶剂化二氯化磷，得到相应的N-类固醇吡啶鎓氯化物。
• A New, Practical and Efficient Method for Protecting Alcohols as tert-Butyl Ethers
  作者：Ernesto Occhiato、Cristina Prandi、Alessandro Barge、Dina Scarpi、Silvia Tabasso、Paolo Venturello

  DOI：10.1055/s-0029-1219360

  日期：2010.3

  A new method for protecting alcohols as tert-butyl ethers is reported. The reaction is performed in tert-butyl acetate in the presence of a catalytic amount of HClO 4 . The process is extremely efficient and primary and secondary alcohols as well as diols are protected under very mild conditions. Remarkably, tert-butyl acetate can be easily recovered after the workup of the reaction and recycled.

  报道了一种将醇类保护为叔丁基醚的新方法。该反应在催化量的HClO 4 存在下在乙酸叔丁酯中进行。该过程非常有效，伯醇和仲醇以及二醇在非常温和的条件下得到保护。值得注意的是，乙酸叔丁酯在反应后很容易回收并循环使用。
• Methods and compositions for the efficient delivery of therapeutic agents to cells and animals
  申请人：Rana M. Tariq

  公开号：US20070260055A1

  公开（公告）日：2007-11-08

  The present invention provides methods of carrying out the safe and reliable preparation of lipids comprising quaternary amines. Such lipids are especially suited for introducing therapeutic agents into cells or organisms. In particular, the lipids of the invention are suitable for the efficient transfer of gene therapy agents into mammalian cells or organisms in a cell type specific or tissue specific manner.

  本发明提供了一种安全可靠的制备含季铵盐脂质的方法。这种脂质特别适合将治疗剂介入细胞或生物体中。特别是，本发明的脂质适用于以细胞类型特异性或组织特异性的方式高效地将基因治疗剂转移到哺乳动物细胞或生物体中。
• Implants for localized drug delivery and methods of use thereof
  申请人：The Regents of the University of California

  公开号：US10912933B2

  公开（公告）日：2021-02-09

  Provided herein is an implant for delivering a hydrophobic active agent to a target tissue. The implant may include a scaffold defining a first surface and a second surface opposite the first surface, wherein the scaffold is substantially impermeable to a hydrophobic active agent, and a silicone tubing having a wall permeable to the active agent, wherein a first length of the silicone tubing is affixed to the first surface of the scaffold, wherein the two ends of the silicone tubing extend from the first surface, and wherein a path outlined by a second length of the tubing within the first length is circuitous. Also provided is a method of using the implant to locally deliver a hydrophobic active agent to a target tissue, and kits that find use in performing the present method.

  本文提供了一种向目标组织输送疏水活性剂的植入物。该植入物可包括界定第一表面和与第一表面相对的第二表面的支架，其中支架基本上不渗透疏水活性剂，以及具有可渗透活性剂壁的硅胶管，其中硅胶管的第一长度贴在支架的第一表面上，其中硅胶管的两端从第一表面延伸，并且第一长度内的第二长度的硅胶管所勾勒的路径是迂回的。此外，还提供了一种使用植入物向目标组织局部递送疏水活性剂的方法，以及可用于实施本方法的试剂盒。