4-(bis(4-methoxyphenyl)(phenyl)methoxy)butan-1-ol | 151171-74-3

• 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: 4-(bis(4-methoxyphenyl)(phenyl)methoxy)butan-1-ol
• 英文别名: 4-[bis(4-methoxyphenyl)(phenyl)methoxy]butan-1-ol；4-[(4,4'-dimethoxytrityl)oxy]butan-1-ol；4-[(4,4'-dimethoxytrityl)oxy]butanol；4-(4,4'-dimethoxytrityl)butan-1-ol；4-[Bis(4-methoxyphenyl)(phenyl)methoxy]-1-butanol；4-[bis(4-methoxyphenyl)-phenylmethoxy]butan-1-ol
• CAS: 151171-74-3
• 化学式: C₂₅H₂₈O₄
• 分子量: 392.495
• InChiKey: WCJDMQVWRNVFRO-UHFFFAOYSA-N

物化性质

• 沸点：
  526.5±50.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 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：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(bis(4-methoxyphenyl)(phenyl)methoxy)butan-1-ol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以42%的产率得到4-[bis(4-methoxyphenyl)phenylmethoxy]butanoic acid
  参考文献：
  名称：

  Optimization and Mechanistic Analysis of Oligonucleotide Cleavage from Palladium-Labile Solid-Phase Synthesis Supports¹

  摘要：

  Pd(0)-labile solid-phase synthesis supports have been used to produce oligonucleotides containing S'-alkyl carboxylic acid and 3'-hydroxy termini in quantitative yields. Optimization of the cleavage reaction conditions using tetrabutylammonium formate buffer resulted in quantitative yields of oligonucleotides using 4 molar equiv of Pd-2(dba)(3).CHCl3 in 1 h at 55 degrees C. A proton source facilitates cleavage of the oligonucleotide from the supports. Trace amounts of water, acting as a nucleophile on the eta(3)-complex, presumably preventing back biting by the initially released oligonucleotide, are required to obtain reproducibly high yields of cleaved oligonucleotides during a 1 h reaction. The previously observed lability of beta-cyanoethyl groups to the Pd(0) conditions has been examined using a mononucleotide substrate. Cleavage of the beta-cyanoethyl group was shown to proceed to the exclusion of other alkyl groups. A mechanism involving initial insertion by Pd(0) into the carbon-oxygen bond of the beta-cyanoethyl group is suggested to account for the cleavage of this group.

  DOI：

  10.1021/jo980135b
• 作为产物：
  描述：

  1,4-丁二醇 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 反应 20.0h， 以87%的产率得到4-(bis(4-methoxyphenyl)(phenyl)methoxy)butan-1-ol
  参考文献：
  名称：

  3-取代尿苷和假尿苷衍生物的合成和溶液构象研究。

  摘要：

  合成了一系列基于天然存在的 3-(3-amino-3-carboxypropyl) 修饰的 3-取代尿苷和假尿苷衍生物。它们的水溶液构象是通过使用圆二色性和核磁共振光谱确定的。显示官能团组成和链长对修饰的核苷的顺/反构象的分布只有细微的影响。决定核苷构象的主要因素似乎是糖苷键（C-与N-糖苷）。

  DOI：

  10.1016/j.bmc.2007.11.039

文献信息

• Tuning DNA Stability To Achieve Turnover in Template for an Enzymatic Ligation Reaction
  作者：Abu Kausar、Rosalie D. McKay、Jade Lam、Rohan S. Bhogal、Alexandra Y. Tang、Julianne M. Gibbs-Davis

  DOI：10.1002/anie.201102579

  日期：2011.9.12

  destabilizing modifications into a DNA template leads to turnover in a DNA‐templated ligation reaction. By incorporating a cross‐catalytic cycle, self‐replication was also achieved, with one target able to make 32 copies of itself (see picture). This destabilization approach represents a general method for incorporating amplification into DNA ligation processes using T4 DNA ligase.

  学会放手：将不稳定的修饰引入DNA模板会导致DNA模板的连接反应的更新。通过整合交叉催化循环，还实现了自我复制，一个目标能够自我复制32个（参见图片）。这种去稳定化方法代表使用T4 DNA连接酶将扩增结合到DNA连接过程中的一般方法。
• Synthesis and solution conformation studies of 3-substituted uridine and pseudouridine derivatives
  作者：Yu-Cheng Chang、Jayatilake Herath、Tony H.-H. Wang、Christine S. Chow

  DOI：10.1016/j.bmc.2007.11.039

  日期：2008.3

  A series of 3-substituted uridine and pseudouridine derivatives, based on the naturally occurring 3-(3-amino-3-carboxypropyl) modification, were synthesized. Their aqueous solution conformations were determined by using circular dichroism and NMR spectroscopy. Functional group composition and chain length were shown to have only a subtle influence on the distribution of syn/anti conformations of the

  合成了一系列基于天然存在的 3-(3-amino-3-carboxypropyl) 修饰的 3-取代尿苷和假尿苷衍生物。它们的水溶液构象是通过使用圆二色性和核磁共振光谱确定的。显示官能团组成和链长对修饰的核苷的顺/反构象的分布只有细微的影响。决定核苷构象的主要因素似乎是糖苷键（C-与N-糖苷）。
• OLIGONUCLEOTIDE DERIVATIVE, OLIGONUCLEOTIDE CONSTRUCT USING THE SAME, AND METHODS FOR PRODUCING THEM
  申请人：GIFU UNIVERSITY

  公开号：US20180094017A1

  公开（公告）日：2018-04-05

  The oligonucleotide derivative of the present invention is represented by Formula (1). This derivative is considered to be introduced into cells by binding of its amino sugar chain moiety to a ligand on cell surfaces, and have selective drug delivery function. The oligonucleotide derivative can be easily synthesized and introduced into cells without using a lipofection reagent. wherein—A and B are independently modified or unmodified oligonucleotides whose total chain length is 3 or more, and A and B do not contain hydroxyl groups at 3′ and 5′ ends of the oligonucleotide; S represents a sugar substituent, a peptide chain, or a tocopherol-binding group; and an alkyl group may be bound instead of hydrogen bound to a benzene ring.

  本发明的寡核苷酸衍生物由式（1）表示。该衍生物被认为通过其氨基糖链部分与细胞表面的配体结合而被引入细胞，并具有选择性药物传递功能。该寡核苷酸衍生物可以在不使用脂质体载体的情况下轻松合成并引入细胞。其中，A和B分别是经修饰或未经修饰的寡核苷酸，其总链长为3或更长，且A和B不含有寡核苷酸的3′和5′末端的羟基；S代表糖取代基、肽链或生育酚结合基；和烷基基团可以与苯环上的氢结合而不是氢结合。
• TFFH as an Excellent Reagent for Acylation of Alcohols, Thiols and Dithiocarbamates
  作者：Jørn B. Christensen、Michael Pittelkow、Fadhil S. Kamounah、Ulrik Boas、Brian Pedersen

  DOI：10.1055/s-2004-831250

  日期：——

  A convenient and easy procedure to synthesize esters and thioesters from the corresponding carboxylic acid using TFFH as the coupling reagent is described. The preparation of N-acyl-dithiocarbamates from carboxylic acids and 1,3-thiazolidine-2-thione with TFFH as the coupling reagent is also described.

  描述了一种使用TFFH作为偶联剂，从相应的羧酸合成酯和硫酯的方便且简单的程序。还描述了使用TFFH作为偶联剂，从羧酸和1,3-噻唑烷-2-硫酮制备N-酰基二硫代氨基甲酸盐的方法。
• Hydroxyalkylated phosphoramidate, phosphoramidothioate and phosphorodiamidothioate derivatives as thiophosphate protecting groups in the development of thermolytic DNA prodrugs
  作者：Andrzej Grajkowski、Jacek Cieślak、Alexei Gapeev、Serge L. Beaucage

  DOI：10.1039/b9nj00692c

  日期：——

  The hydroxyalkylated phosphoramidate 4a, phosphoramidothioates 4b, 4e–j, and phosphorodiamidothioates 4c and 4d have been identified as a new class of heat-sensitive thiophosphate protecting groups in the development of thermolytic immunomodulatory DNA prodrugs. These alcohols are converted to their deoxyribonucleoside phosphoramidite derivatives 6a–j, which are then used in the preparation of the thermosensitive dinucleoside phosphorothioates 7a–j. The negatively charged thiophosphate protecting groups of 7a–b and 7e–j presumably undergo thermolytic cyclodeesterification at elevated temperature under essentially neutral conditions. The thiophosphate protecting groups of 7e and 7f show relatively rapid deprotection kinetics at 37 °C (t½ = 20 and 42 h, respectively) and are therefore suitable for the protection of phosphodiester functions flanking the CpG motifs of immunomodulatory DNA sequences, whereas the thiophosphate protecting groups of 7g–j with thermolytic deprotection half-lives in the range of 94–265 h at 37 °C are more appropriate for the thiophosphate protection of CpG motifs. Furthermore, the thermostability of the group protecting the thiophosphate function of 7a (t½ = 82 min at 90 °C) should offer adequate protection of the 5′- and/or 3′-terminal phosphodiester functions of DNA prodrugs against ubiquitous extracellular and intracellular exonucleases.

  羟基烷基磷酰胺盐（4a）、磷酰胺硫酸酯（4b、4e–j）和磷酸二酰胺硫酸酯（4c和4d）被确定为在热解免疫调节DNA前药开发中一种新的热敏硫酸酯保护基。这些醇类转化为其脱氧核糖核苷磷酰胺酸酯衍生物（6a–j），然后用于制备热敏的二核苷酸磷硫酸酯（7a–j）。7a-b和7e-j的带负电荷的硫酸酯保护基在基本中性条件下的高温下，可能经历热解环酯化。7e和7f的硫酸酯保护基在37 °C下显示出相对快速的去保护动力学（半衰期分别为20小时和42小时），因此适合于保护免疫调节DNA序列中CpG基序两侧的磷酸二酯功能，而7g–j的硫酸酯保护基在37 °C下的热解去保护半衰期为94–265小时，更适合用于CpG基序的硫酸酯保护。此外，7a中保护硫酸酯功能的保护基在90 °C下的热稳定性（半衰期为82分钟）应能有效保护DNA前药的5′和/或3′端磷酸二酯功能，免受普遍存在的细胞外和细胞内外切酶的影响。