3β-O-(1',2':3',4'-di-O-isopropylidene-α-D-galactopyranos-6'-yl)cholest-5-ene | 1232680-84-0

• 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: 3β-O-(1',2':3',4'-di-O-isopropylidene-α-D-galactopyranos-6'-yl)cholest-5-ene
• 英文别名: (1S,2R,6R,8R,9S)-8-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxymethyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 1232680-84-0
• 化学式: C₃₉H₆₄O₆
• 分子量: 628.934
• InChiKey: QQFSIWSGCHTHMG-PANDIKFESA-N

物化性质

• 熔点：
  145-148 °C(Solv: hexane (110-54-3); dichloromethane (75-09-2))
• 沸点：
  649.4±55.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  cholest-5-en-3β-yl diphenyl phosphate 在 四氮唑 、 tetrabutylammonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 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

文献信息

• 3α,5α-Cyclocholestan-6β-yl ethers as donors of the cholesterol moiety for the electrochemical synthesis of cholesterol glycoconjugates
  作者：Aneta M Tomkiel、Adam Biedrzycki、Jolanta Płoszyńska、Dorota Naróg、Andrzej Sobkowiak、Jacek W Morzycki

  DOI：10.3762/bjoc.11.16

  日期：——

  3α,5α-Cyclocholestan-6β-yl alkyl and aryl ethers were proved to be efficient cholesteryl donors in the electrochemical synthesis of glycoconjugates. 3α,5α-Cyclocholestan-6β-ol (i-cholesterol) and its tert-butyldimethylsilyl ether can also be used for this purpose. The i-cholesterol derivatives show similar reactivities to those of previously studied 3α,5α-cyclocholestan-6β-thioethers.

  3α,5α-环胆甾烷-6β-基烷基和芳基醚被证明是在糖脂共轭物的电化学合成中高效的胆固醇供体。3α,5α-环胆甾烷-6β-醇（i-胆固醇）及其tert-丁基二甲基硅醚也可用于此目的。i-胆固醇衍生物显示出与先前研究的3α,5α-环胆甾烷-6β-硫醚类似的反应性。
• Electrochemical synthesis of glycoconjugates of 3β-hydroxy-Δ5-steroids by using non-activated sugars and steroidal thioethers
  作者：Aneta M. Tomkiel、Krzysztof Brzezinski、Zenon Łotowski、Leszek Siergiejczyk、Piotr Wałejko、Stanisław Witkowski、Jan Kowalski、Jolanta Płoszyńska、Andrzej Sobkowiak、Jacek W. Morzycki

  DOI：10.1016/j.tet.2013.07.106

  日期：2013.10

  electrochemical synthesis of glycoconjugates is presented. Thioether derivatives of cholesterol and other sterols were subjected to anodic oxidation in the presence of a sugar alcohol affording glycoconjugates with the sugar linked to a steroid moiety by an ether bond. The isomeric 6β-3α,5α-cyclo-steroidal thioethers proved to be better sterol donors than the normal 3β-Δ5-steroidal thioethers.

  对于糖缀合物的电化学合成一个新的协议，提出。胆固醇和其它甾醇的硫醚衍生物的糖醇，得到与通过醚键连接至类固醇部分的糖的糖缀合物的存在下进行阳极氧化。同分异构的6β-3α，5α-环-steroidal硫醚被证明是更好的固醇捐助者比正常3β-Δ 5 -steroidal硫醚。
• A selective electrochemical method of glycosylation of 3β-hydroxy-Δ5-steroids
  作者：Jacek W. Morzycki、Zenon Łotowski、Leszek Siergiejczyk、Piotr Wałejko、Stanisław Witkowski、Jan Kowalski、Jolanta Płoszyńska、Andrzej Sobkowiak

  DOI：10.1016/j.carres.2010.03.018

  日期：2010.5

  A new electrochemical glycosylation method is presented. According to the method cholesterol and other 3beta-hydroxy-Delta(5)-steroids can be selectively transformed to glycosides using non-activated sugars. The method is also useful for the synthesis of glycoconjugates with sugar linked to a steroid moiety by an ether bond.

  提出了一种新的电化学糖基化方法。根据该方法，可以使用非活化糖将胆固醇和其他3β-羟基-Delta（5）-类固醇选择性地转化为糖苷。该方法还可用于合成具有通过醚键与甾体部分连接的糖的糖缀合物。
• A Strain-Promoted Divergent Chemical Steroidation Unveils Potent Anti-Inflammatory Pseudo-Steroidal Glycosides
  作者：Han Ding、Xiao-Lin Zhang、Aoxin Guo、Qian Ping Lee、Chao Cai、Ming Li、Hongzhi Cao、Xue-Wei Liu

  DOI：10.1021/jacs.4c00537

  日期：2024.5.1

  of the regioselectivity, underlying an acceptor-dependent steroidation mode. This approach can be readily extended to the etherification of sugar alcohols to enable the achievement of a diversity-oriented, pipeline-like synthesis of pseudo-steroidal glycosides in good to excellent yields with complete stereo- and regiospecific control for anti-inflammatory agent discovery. Immunological studies have

  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。