5'-O-(4,4'-dimethoxytrityl)thymidine-3'-O-(2-chlorophenyl)phosphate triethylammonium salt | 85393-37-9

• 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: 5'-O-(4,4'-dimethoxytrityl)thymidine-3'-O-(2-chlorophenyl)phosphate triethylammonium salt
• 英文别名: 5'-O-(dimethoxytrityl)thymidine 3'-(o-chlorophenyl) phosphate triethylammonium salt；2-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphate triethylammonium salt；5'-O-(4,4'-dimethoxytriphenylmethyl)thymidine-3'-O-(2-chlorophenyl)phopsphate；triethylammonium<5'-O-DMT-thymidine-3'-O-(2-chlorophenyl)phosphate>；5'-O-(bis(4-methoxyphenyl)phenylmethyl)-3'-thymidylic acid, mono(2-chlorophenyl) ester, compd. with N,N-diethylethanamine (1:1)；2-chlorophenyl-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphate triethylamine salt；Einecs 286-938-3；[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (2-chlorophenyl) hydrogen phosphate;N,N-diethylethanamine
• CAS: 85393-37-9
• 化学式: C₆H₁₅N*C₃₇H₃₆ClN₂O₁₀P
• 分子量: 836.319
• InChiKey: MJFDEDRWCWOABG-CFNLNGMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  58
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)thymidine-3'-O-(2-chlorophenyl)phosphate triethylammonium salt 在 铜 、 锌 吡啶 、 N₁,N₁,N₃,N₃-tetramethylguanidinum 2-nitrobenzaldoximate 、 苯甲基-2-磺酰三硝基三氮唑 、 三乙胺 、 三氯乙酸 作用下， 以 1,4-二氧六环 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Napoli, Lorenzo De; Montesarchio, Daniela; Piccialli, Gennaro, Gazzetta Chimica Italiana, 1991, vol. 121, # 8, p. 419 - 421

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯苯基二氯膦 在 1H-1,2,4-三唑 、 N-甲基咪唑 、 水 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 5'-O-(4,4'-dimethoxytrityl)thymidine-3'-O-(2-chlorophenyl)phosphate triethylammonium salt
  参考文献：
  名称：

  Straightforward Synthesis of Lipophilic Thymidine Glucopyranosyl Monophosphates as Models for a Drug Delivery System Across Cellular Membranes

  摘要：

  O-methyl (3'-6) and (5'-6) thymidinyl gluco- and mannopyranosides and (3'-6) thymidinyl glucofuranose can be synthesised in excellent yields by applying the phosphotriester method. The lipophilic phosphotriesters thus obtained are designed as carriers of nucleoside drugs across cellular membranes.

  DOI：

  10.1080/07328319908044627

文献信息

• Improved Synthesis of Oligodeoxyribonucleotides by Solid-Phase Phosphotriester Method UtilizingO6-[2-(p-Nitrophenyl)ethyl]-2?-deoxyguanosine Derivatives
  作者：Andr� Chollet、Edgar Ayala、Eric H. Kawashima

  DOI：10.1002/hlca.19840670521

  日期：1984.8.8

  The synthesis of oligodeoxyribonucleotides on a cross-linked polystyrene solid support utilizing stable mono- and dinucleotide phosphotriester building blocks is presented. The use of O6[2-(p-nitrophenyl)ethyl]-2′-deoxyguanosine derivatives yields cleaner DNA fragments by suppressing side reactions. Modifications improving the phosphotriester methodology are presented. The purification methods and

  提出了利用稳定的单核苷酸和二核苷酸磷酸三酯结构单元在交联的聚苯乙烯固体载体上合成寡脱氧核糖核苷酸。使用ö 6 [2-（p通过抑制副反应硝基苯基）乙基] -2'-脱氧鸟苷的产率衍生物吸尘器的DNA片段。提出了改进磷酸三酯方法的修饰。描述了合成寡聚脱氧核糖核苷酸的纯化方法和分析。
• Efficient and flexible access to fully protected trinucleotides suitable for DNA synthesis by automated phosphoramidite chemistry
  作者：Andrea Zehl、Antje Starke、Dieter Cech、Thomas Hartsch、Rainer Merkl、Hans-Joachim Fritz

  DOI：10.1039/cc9960002677

  日期：——

  An efficient synthetic approach to protected trinuclotide phosphoramidites suitable for codon-by-codon synthesis of structural gene combinatorial libraries is described; the procedure rests on the use of pair of orthogonal protecting groups for the two oligomer termini and offers flexibility in the choice of chain elongation direction going from dimer to trimer.

  本文介绍了一种高效的三核苷酸磷酰胺保护合成方法，适用于逐个密码子合成结构基因组合文库；该方法的基础是在两个寡聚体末端使用一对正交的保护基团，并可灵活选择从二聚体到三聚体的链延伸方向。
• Naphthaloyl group: a new selective amino protecting group for deoxynucleosides in oligonucleotide synthesis
  作者：Archana Dikshit、Manjula Chaddha、R. K. Singh、Krishna Misra

  DOI：10.1139/v88-464

  日期：1988.12.1

  The naphthaloyl group has been found to be a selective amino protecting group for deoxycytidine, deoxyadenosine, and deoxyguanosine in oligodeoxyribonucleotide synthesis. All three protected monomers obtained (78–85%), being six-membered cyclic imides, were fairly stable. These protected monomers were used successfully for the preparation of dimers (phosphodiester approach) and tetramers (phosphotriester approach) in solution as well as solid phase, respectively. The group acted as a purification tool due to its high lipophilicity. No adverse effect has been observed either on the glycosidic bond (depurination) or the internucleotidic bond during its removal. The monomeric units were characterized by UV, NMR, and elemental analyses whereas the tetramers were characterized by enzymatic hydrolyses with snake venom phosphodiesterase followed by alkaline phosphatase.

  萘酰基团已被发现是脱氧胞苷、脱氧腺苷和脱氧鸟苷在寡脱氧核糖核苷酸合成中的选择性氨基保护基团。所得到的三种保护单体（78-85%），均为六元环亚酰胺，相当稳定。这些保护单体成功地用于溶液相和固相分别制备二聚体（磷酸二酯途径）和四聚体（磷酸三酯途径）。该基团由于其高亲脂性而作为一种纯化工具。在其去除过程中，既没有观察到对糖苷键（去嵌合）的不良影响，也没有观察到对核苷酸间键的不良影响。单体单位通过紫外线、核磁共振和元素分析进行了表征，而四聚体通过蛇毒磷酸二酯酶酶解后接碱性磷酸酶进行了表征。
• The Photochemistry of Thymidylyl-(3′-5′)-5-methyl-2′-deoxycytidine in Aqueous Solution¶
  作者：Lech Celewicz、Moriz Mayer、Martin D. Shetlar

  DOI：10.1562/2004-06-15-ra-201.1

  日期：——

  adduct and its related Dewar isomer, and two isomers of a product in which the m5C moiety was converted into an acrylamidine. Small amounts of thymidylyl-(3′-5′)-thymidine (TpT) were also formed, presumably as a secondary photoreaction product. In addition, a photoproduct was characterized in which the m5C moiety was lost, thus generating 3′-thymidylic acid esterified with 2′-deoxyribose at the 5-hydroxyl

  摘要 使用 254 nm 和 UV-B 辐射在水溶液中研究了二核苷单磷酸胸苷基-(3'-5')-5-甲基-2'-脱氧胞苷 (Tpm5dC) 的光化学。多种含有 5-甲基胞嘧啶 (m5C) 的二核苷酸光产物已被分离和表征。其中包括两种环丁烷二聚体 (CBD)（顺式-syn [c,s] 和反式-syn 形式）、一个 (6-4) 加合物及其相关的杜瓦异构体，以及一种产品的两种异构体，其中 m5C 部分是转化为丙烯酰胺。还形成了少量胸苷基-(3'-5')-胸苷 (TpT)，可能是二次光反应产物。此外，光产物的特征在于其中 m5C 部分丢失，从而生成 3'-胸苷酸，在糖部分的 5-羟基上被 2'-脱氧核糖酯化。C、Tpm5dC 的 CBD 很容易脱氨基形成 TpT 的相应 CBD。已经研究了这种脱氨过程的动力学；在 pH 7.4 下，反应的相应活化焓和熵分别为 73.4 kJ/mol 和 -103.5
• EP1710249
  申请人：——

  公开号：——

  公开（公告）日：——