6-(trityloxy)hexan-1-ol | 38257-95-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 6-(trityloxy)hexan-1-ol
• 英文别名: 6-Trityloxy-hexan-1-ol；6-trityloxyhexan-1-ol
• CAS: 38257-95-3
• 化学式: C₂₅H₂₈O₂
• 分子量: 360.496
• InChiKey: AERZGVLBQUEBLP-UHFFFAOYSA-N

物化性质

• 沸点：
  483.5±33.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(trityloxy)hexan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成 6-trityloxyhexanal
  参考文献：
  名称：

  New Antibacterial Agents Derived from the DNA Gyrase Inhibitor Cyclothialidine

  摘要：

  Cyclothialidine (1, Ro 09-1437) is a potent DNA gyrase inhibitor that was isolated from Streptomyces filipinensis NR0484 and is a member of a new family of natural products. It acts by competitively inhibiting the ATPase activity exerted by the B subunit of DNA gyrase but barely exhibits any growth inhibitory activity against intact bacterial cells, presumably due to insufficient permeation of the cytoplasmic membrane. To explore the antibacterial potential of 1, we developed a flexible synthetic route allowing for the systematic modification of its structure. From a first set of analogues, structure-activity relationships (SAR) were established for different substitution patterns, and the 14-hydroxylated, bicyclic core (X) of 1 seemed to be the structural prerequisite for DNA gyrase inhibitory activity. The variation of the lactone ring size, however, revealed that activity can be found among 11- to 16-membered lactones, and even seco-analogues were shown to maintain some enzyme inhibitory properties, thereby reducing the minimal structural requirements to a rather simple, hydroxylated benzyl sulfide (XI). On the basis of these "minimal structures" a modification program afforded a number of inhibitors that showed in vitro activity against Gram-positive bacteria. The best activities were displayed by 14-membered lactones, and representatives of this subclass exhibit excellent and broad in vitro antibacterial activity against Gram-positive pathogens, including Staphylococcus aureus, Streptococcus pyogenes, and Enterococcus faecalis, and overcome resistance against clinically used drugs. By improving the pharmacokinetic properties of the most active compounds (94, 97), in particular by lowering their lipophilic properties, we were able to identify congeners of cyclothialidine (1) that showed efficacy in vivo.

  DOI：

  10.1021/jm0310232
• 作为产物：
  描述：

  6-trityloxyhexanal 在 Sodium Tris(1,1,1,3,3,3-hexafluoroisopropoxy)borohydride 作用下， 以 四氢呋喃 、 hexafluoropropan-2-ol 为溶剂， 反应 5.0h， 以91%的产率得到6-(trityloxy)hexan-1-ol
  参考文献：
  名称：

  三（六氟异丙氧基）硼氢化钠对酮的醛类化学选择性还原

  摘要：

  使用可作为 THF 溶液储存的三（六氟异丙氧基）硼氢化钠，在酮的存在下实现醛的化学选择性还原。

  DOI：

  10.1055/s-2008-1078217

文献信息

• Synthesis of Tethered Trisaccharides To Probe Inter-Saccharide Flexibility in Carbohydrate−Protein Interactions
  作者：Ramon Alibés、David R. Bundle

  DOI：10.1021/jo9806097

  日期：1998.9.1

  Two crystal structures of the trisaccharide epitope alpha-D-Galp(1-->2)[alpha-D-Abep(1-->3)alpha-D-Manp1-->OCH(3) 1 bound to antibody Fab and single-chain Fv fragments have been used to guide the design of an intramolecular tether that constrains the trisaccharide ligand to conformations close to those of the bound state. Preorganization of the ligand should overcome entropic penalties to binding and

  三糖表位的两个晶体结构alpha-D-Galp（1-> 2）[alpha-D-Abep（1-> 3）alpha-D-Manp1-> OCH（3）1与抗体Fab和单链Fv片段已用于指导分子内束缚的设计，该束缚将三糖配体约束为接近结合态的构象。配体的预组织应克服对结合的熵罚并提供增强的亲和力。使用三个系链[O（CH（2））（n）（）O，n = 6、7和8]固定甘露糖和半乳糖残基的溶剂暴露C6原子。使用了两种合成方案。第一种使用带有被保护为三苯甲基醚6-8的系链的1-硫代半乳糖苷乙基。供体6-8中的任何一个在C6处含有甲磺酸盐的甘露吡喃糖苷5的糖基化得到二糖37-39。随后除去三苯甲基，允许在系链的ω-羟基上生成醇盐，以38％的收率置换磺酸盐。通过比较，当掺入ω-甲磺酰氧基系绳作为甘露糖苷9时，与半乳糖基供体10反应后的二糖产物52以61％的产率转化为大环4。通过硫代糖苷化学法引入3，6-二脱氧
• A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation
  作者：Wangkhem P Singh、Rajkumar S Singh

  DOI：10.3762/bjoc.13.17

  日期：——

  formation is likely to be mediated by hydrophobic interactions between the triphenylmethyl moieties and alkyl chains. Possible self-assembled packing arrangements in the gel state for 1,8-bis(trityloxy)octane and (hexadecyloxymethanetriyl)tribenzene are presented. Results from this study strongly indicate that triphenylmethyl group is a promising gelling structural unit which may be further exploited

  在目前的工作中，我们已经探索了三苯甲基（一种通常用于伯醇的保护基）作为分子胶凝剂设计中的胶凝结构组分的用途。我们合成了一个简单的伯醇三苯甲基衍生物的小型文库，并研究了它们在不同溶剂中的胶凝特性。一些衍生物的胶凝效率为中等至极好，最小胶凝浓度为0.5-4.0％w / v，凝胶-溶胶转变温度范围为31-75°C。1,8-双（三苯甲氧基）辛烷，1,8-辛二醇的二三苯甲基衍生物是最有效的有机胶凝剂。凝胶的详细表征使用扫描电子显微镜，FTIR光谱，流变学和粉末XRD技术进行。该凝胶对水溶性染料也显示出良好的吸收特性。考虑到该分子的非极性性质，凝胶形成很可能是由三苯基甲基部分和烷基链之间的疏水相互作用介导的。给出了凝胶状态下1,8-双（三苯甲氧基）辛烷和（十六烷氧基甲三基）三苯的可能的自组装堆积安排。这项研究的结果强烈表明，三苯基甲基是一种很有前途的胶凝结构单元，可以在基于小分子的胶凝剂的设计中进一步
• Alternative Reagents for the Tritylation of Alcohols
  作者：Y. Jyothi、A. K. Mahalingam、A. Ilangovan、G. V. M. Sharma

  DOI：10.1080/00397910701357833

  日期：2007.6

  Abstract Two new tritylation reagents [viz. p‐methoxybenzyl trityl ether (p‐MBTE) and prenyl trityl ether (PTE)] were prepared. These two new reagents were utilized efficiently for the tritylation of alcohols, using DDQ or 20 mol% DDQ–3 eq. Mn(OAc)3.

  摘要 两种新的三苯甲基化试剂 [即。制备了对甲氧基苄基三苯甲基醚（p-MBTE）和异戊二烯基三苯甲基醚（PTE）]。这两种新试剂有效地用于醇的三苯甲基化，使用 DDQ 或 20 mol% DDQ–3 eq。Mn(OAc)3。
• Influence of the spacer length on the phase behaviors of mesogen-jacketed liquid crystalline polymers with a bulk side-chain
  作者：Yongbing Luo、Sheng Chen、Hailiang Zhang

  DOI：10.1039/c5ra07155k

  日期：——

  all the polymers exhibited excellent thermal stabilities. The liquid crystalline (LC) phase structures and behaviors of the polymers were strongly dependent on the spacer length (m). With the increase of m, Tg of Pv-m-Tr decreased from 116.7 °C to 11.5 °C because of the alkyl plasticization. When m = 2, 4, 6, 8, 10, the Pv-m-Tr formed a stable columnar nematic (ΦN) phase above Tg. When m = 12, the Pv-12-Tr

  一系列在侧链上包含两个三苯甲基（Tr）单元的介晶包覆液晶聚合物（MJLCP），称为聚2,5-双[（三苯甲氧基-烷基）氧羰基]-苯乙烯}（表示为Pv- m设计并成功地通过自由基聚合合成了-Tr，m＝2、4、6、8、10、12，这是对苯二甲酸酯核与侧链中的Tr部分之间的亚甲基单元的数目。单体的化学结构通过1 H NMR和质谱确认。用1对聚合物进行分子表征1 H NMR，GPC和TG分析。通过包括DSC，POM和1D / 2D WAXD在内的多种技术研究了聚合物的相结构和转变温度。实验结果表明，所有聚合物均表现出优异的热稳定性。聚合物的液晶（LC）相结构和行为在很大程度上取决于间隔物长度（m）。用的增加米，Ť克PV-的米-Tr从116.7℃降至11.5℃，因为烷基塑化。当米= 2，4，6，8，10，PV-米-Tr形成稳定的柱状向列型（Φ Ñ）相以上Ť克。当m = 12时，Pv-12-Tr在T
• Design, Synthesis and Structural Analysis of Glucocerebrosidase Imaging Agents
  作者：Rhianna J. Rowland、Yurong Chen、Imogen Breen、Liang Wu、Wendy A. Offen、Thomas J. Beenakker、Qin Su、Adrianus M. C. H. Nieuwendijk、Johannes M. F. G. Aerts、Marta Artola、Herman S. Overkleeft、Gideon J. Davies

  DOI：10.1002/chem.202102359

  日期：2021.11.25

  Tagged cyclophellitols offer a powerful activity-based probe (ABP) approach to the study of glycosidase activities. Here, a range of cyclophellitol epoxide and aziridine inhibitors and ABPs were synthesised and investigated on the 3D structure of human β-glucocerebrosidase (GBA), demonstrating their mechanism-based mode of action. We envisage these inactivators will serve useful in the study of GBA

  标记的环酚为研究糖苷酶活性提供了一种强大的基于活性的探针 (ABP) 方法。在这里，合成了一系列环酚醇环氧化物和氮丙啶抑制剂和 ABP，并研究了人类 β-葡萄糖脑苷脂酶 (GBA) 的 3D 结构，证明了它们基于机制的作用模式。我们设想这些灭活剂将有助于研究与戈谢病相关的 GBA。