2-O-(4,4'-dimethoxytrityl)-1-hydroxyethane | 110675-03-1

• 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: 2-O-(4,4'-dimethoxytrityl)-1-hydroxyethane
• 英文别名: 2-(bis(4-methoxyphenyl)(phenyl)methoxy)ethanol；2-[bis(4-methoxyphenyl)phenylmethyloxy]ethanol；2-(bis(4-methoxyphenyl)(phenyl)methoxy)ethan-1-ol；1-(4,4'-dimethoxytrityloxy)ethan-2-ol；2-(4,4'-dimethoxytrityl)-ethyleneglycol；2-[(4,4'-dimethoxytrityl)oxy]ethan-1-ol；2-(4,4'-dimethoxytrityloxy)ethanol；O-dimethoxytrityl ethylene glycol；2-[bis(4-methoxyphenyl)-phenylmethoxy]ethanol
• CAS: 110675-03-1
• 化学式: C₂₃H₂₄O₄
• 分子量: 364.441
• InChiKey: NUEYEOPTRDUJFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  509.9±50.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  2-O-(4,4'-dimethoxytrityl)-1-hydroxyethane 在 咪唑 、 三乙胺 、 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Properties of Combinatorial Libraries of Phosphoramidates

  摘要：

  We have assembled a set of combinatorial libraries of phosphoramidates for pharmacological evaluation. A range of functionalized and unfunctionalized diols, representing a variety of diversity elements, were converted into their corresponding dimethoxytrityl H-phosphonate derivatives which were coupled to each other to produce H-phosphonate dimers and trimers. The H-phosphonate diesters were converted into phosphoramidates by reaction with a wide range of primary and secondary amines. Very large libraries (theoretically, in excess of one million compounds) possessing five sites of diversity were generated for use in our drug discovery program. Smaller libraries with lower molecular weights were also prepared in which only two monomeric units were coupled together and converted into their phosphoramidate derivatives. Methods for the attachment of both radioactive and nonradioactive labels, including (32)phosphorus, tritium, and fluorescein, have been developed. Representative single sequences were also prepared and their chemical properties studied.

  DOI：

  10.1021/jo960192+
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙二醇 为溶剂， 以47%的产率得到2-O-(4,4'-dimethoxytrityl)-1-hydroxyethane
  参考文献：
  名称：

  MELANIN PRODUCTION INHIBITOR

  摘要：

  披露了一种黑色素生产抑制剂，它对黑色素的生产具有出色的抑制活性且高度安全。该黑色素生产抑制剂包括由通用公式（1）表示的化合物（不包括克霉唑）和/或其药理上可接受的盐。在公式中，A1、A2和A3独立地选自氢原子、可能带有取代基的芳基团和可能带有取代基的芳香杂环团，其中至少A1、A2和A3之一选自芳基团和芳香杂环团，A1、A2和A3中包含的碳原子总数为6至50，并且当至少两个A1、A2和A3表示芳基团或芳香杂环团时，相邻的两个芳基或芳香杂环团可以通过烷基链或烯基链相互连接形成环；m代表0至2的整数；X代表异原子、氢原子或碳原子；R1和R2独立地选自氢原子和氧代基，其中当R1和R2之一是氧代基时，另一个不出现；R3选自氢原子和C 1-8 碳氢化合物组，其中一些或所有的氢原子或碳原子可能被异原子或异原子取代，其中化合物中存在的R3的数量对应于X的数量，并且当存在两个或更多R3时，R3独立地存在，并且相邻的两个R3可以相互连接以与X一起形成环，并且R3的末端可以与A1、A2和A3连接的碳原子结合，从而形成环。

  公开号：

  US20110243865A1

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。
• Modified oligodeoxyribonucleoditides
  申请人：Sankyo Company, Limited

  公开号：US05674856A1

  公开（公告）日：1997-10-07

  Compounds for the treatment or prophylaxis of a viral infection in a mammal, which may be human, are provided. The compounds are oligodeoxyribonucleic acid derivatives, and a novel route to such compounds is also provided together with intermediates of more general utility. The active compounds are of the general formula (1): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are hydrogen atoms, alkyl groups, aryl groups as defined, and anthraquinonyl groups as defined; Z is carbon or silicon; or R.sub.2, R.sub.3 and Z together represent fluorenyl or xanthenyl; R.sub.4 is a hydrogen atom, an alkyl group as defined, an aryl group as defined; Y.sub.1, Y.sub.3 and Y.sub.4 are oxygen, sulfur or >NH; Y.sub.2 is oxygen, sulfur, >NH, alkylene or phenylene; X is alkylene group as defined; m and n are 0 to 10; and B is an oligodeoxyribonucleotide of chain length 3 to 9; or salts thereof.

  提供用于治疗或预防哺乳动物（可能是人类）病毒感染的化合物。这些化合物是寡脱氧核糖核酸衍生物，并提供了一种新颖的合成这些化合物的途径，以及更普遍有用的中间体。活性化合物的一般结构式为（1）：其中R.sub.1、R.sub.2和R.sub.3是氢原子、烷基、所定义的芳基和蒽醌基；Z是碳或硅；或者R.sub.2、R.sub.3和Z一起代表芴基或蒽基；R.sub.4是氢原子、所定义的烷基、所定义的芳基；Y.sub.1、Y.sub.3和Y.sub.4是氧、硫或>NH；Y.sub.2是氧、硫、>NH、烷基或苯基；X是所定义的烷基；m和n为0至10；B是链长为3至9的寡脱氧核糖核苷酸；或其盐。
• OLIGONUCLEOTIDE HAVING NON-NATURAL NUCLEOTIDE AT 5'-TERMINAL THEREOF
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：US20170354673A1

  公开（公告）日：2017-12-14

  An oligonucleotide having a nucleotide residue or a nucleoside residue represented by formula (I) wherein X 1 is an oxygen atom or the like, R 1 is formula (IIA) (wherein R 5A is halogen or the like, and R 6A is a hydrogen atom or the like), formula (IVA) (wherein Y 3A is a nitrogen atom or the like, and Y 4A is CH or the like), or the like, R 2 is a hydrogen atom, hydroxy, halogen, or optionally substituted lower alkoxy, and R 3 is a hydrogen atom or the like, or formula (VI) (wherein n2 is 1, 2 or 3)} at the 5′ end thereof, wherein the nucleotide residue or the nucleoside residue binds to an adjacent nucleotide residue through the oxygen atom at position 3, is provided.

  具有由式(I)表示的核苷酸残基或核苷酸残基的寡核苷酸其中X1是氧原子或类似物，R1是式(IIA)（其中R5A是卤素或类似物，而R6A是氢原子或类似物），式(IVA)（其中Y3A是氮原子或类似物，而Y4A是CH或类似物），或类似物，R2是氢原子，羟基，卤素，或可选择地取代的较低烷氧基，而R3是氢原子或类似物，或式(VI)（其中n2为1、2或3）}在其5'端，其中核苷酸残基或核苷酸残基通过位于位置3的氧原子与相邻核苷酸残基结合。
• A new approach for the synthesis of N-β-enaminocarbonyl 2-oxazolidinones through ring transformation reactions of uracil
  作者：Yoshiaki Kitamura、Yuto Ohshima、Yuki Nagaya

  DOI：10.1016/j.tetlet.2021.153554

  日期：2022.1

  The reaction of N1-sulfonyluracil derivatives bearing a 2-hydroxyethyl moiety at the 3-position with NaH under anhydrous conditions at room temperature affords the corresponding 2-oxazolidinone bearing the β-enaminocarbonyl moiety. These products are useful diversifiable precursors toward various β-amino acids and N-heterocyclic compounds.

  在室温、无水条件下，在 3-位带有 2-羟乙基部分的N 1-磺酰尿嘧啶衍生物与 NaH 反应得到相应的带有 β-烯氨基羰基部分的 2-恶唑烷酮。这些产品是各种 β-氨基酸和N-杂环化合物的有用的多样化前体。
• 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。