1-(2'-deoxy-3'-O-mesyl-5'-O-4,4'-dimethoxytrityl-β-D-threo-pentofuranosyl)-thymine | 143527-01-9

• 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: 1-(2'-deoxy-3'-O-mesyl-5'-O-4,4'-dimethoxytrityl-β-D-threo-pentofuranosyl)-thymine
• 英文别名: 1-[5'-O-(4,4'-dimethoxytrityl)-3'-O-mesyl-2'-deoxy-β-D-furanosyl]thymine；Mes(-3)[DMT(-5)]2-deoxy-D-thrPenf(b)-thymin-1-yl；[(2R,3R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] methanesulfonate
• CAS: 143527-01-9
• 化学式: C₃₂H₃₄N₂O₉S
• 分子量: 622.696
• InChiKey: CSSBLGFIJWFQNH-MPFGFTFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2'-deoxy-3'-O-mesyl-5'-O-4,4'-dimethoxytrityl-β-D-threo-pentofuranosyl)-thymine 在 sodium hydroxide 、 triethylamine trihydrofluoride 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((((2S,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl)disulfaneyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Dinucleoside Monophosphate Analogues Containing Disulfide Linkages

  摘要：

  Two dinucleoside monophosphate analogues containing disulfide linkages (1 and 2) have been prepared for incorporation into oligonucleotides. The modified oligomers will be tested for their potential as antisense agents.

  DOI：

  10.1080/07328319708006228
• 作为产物：
  描述：

  保护胸苷 在 吡啶 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 1-(2'-deoxy-3'-O-mesyl-5'-O-4,4'-dimethoxytrityl-β-D-threo-pentofuranosyl)-thymine
  参考文献：
  名称：

  探讨修饰核苷与 DNA 核酸酶 SNM1A 的结合要求

  摘要：

  SNM1A 是一种涉及 DNA 链间交联修复的核酸酶，因此，它的抑制作用对于克服对化学治疗性交联剂的抗性很重要。然而，SNM1A活性位点中金属离子的数量和身份仍未得到证实，迄今为止报道的抑制剂数量有限。在此，我们报告了基于丙二酸的修饰核苷家族的合成和评估，以研究金属结合基团在核苷衍生的 SNM1A 抑制剂中的最佳定位。这些化合物包括酯、羧酸酯和异羟肟酸丙二酸酯衍生物，它们安装在胸苷的 5'-位或 3'-位或作为两个核苷之间的连接。作为重组 SNM1A 抑制剂的评估表明，所测试的 12 种化合物中有 9 种在 1 mM 浓度下具有抑制作用。最有效的化合物在 5'-位含有异羟肟酸丙二酸酯基团。总体而言，我们的研究促进了对 SNM1A 核苷衍生抑制剂要求的理解，并表明在金属螯合剂（如异羟肟酸丙二酸酯）附近含有带负电荷基团的基团是抑制剂设计中很有前景的结构。

  DOI：

  10.3390/molecules26020320

文献信息

• Labelling compounds for the simple synthesis of 3'-(18f)fluoro-3'-deoxy thymidine and a method for the production thereof
  申请人：——

  公开号：US20040110720A1

  公开（公告）日：2004-06-10

  The application relates to compounds that are suitable as labelable precursors for synthesis of 3′-[ 18 F]fluoro-3′-deoxythymidine and that have formula (1), 1 in which R denotes triphenylmethyl, triphenylmethyl substituted in the phenyl group, trialkylmethyl, triphenylsilyl, triphenylsilyl substituted in the phenyl group, or trialkylsilyl, R′ denotes R 1 —SO 2 , where R 1 is an unsubstituted or substituted C 1 to C 5 alkyl or an unsubstituted or substituted phenyl, and R″ denotes C 2 to C 10 alkyloxycarbonyl, with the exception of 3-N-Boc-1-(3-O-nosyl-5-O-trityl-2-deoxy-&bgr;-D-lyxofuranosyl)thymine. The application also relates to a method for preparation of these compounds and to the use of the same for synthesis of 3′-[ 18 F]fluoro-3′-deoxythymidine.

  该申请涉及适用作为可标记前体的化合物，用于合成3′-[18F]氟-3′-脱氧胸苷，并具有以下化学式（1），其中R代表三苯甲基、苯基上取代的三苯甲基、三烷基甲基、三苯基硅基、苯基上取代的三苯基硅基或三烷基硅基，R′代表R1-SO2，其中R1是未取代或取代的C1到C5烷基或未取代或取代的苯基，R″代表C2到C10烷氧羰基，除了3-N-Boc-1-(3-O-nosyl-5-O-trityl-2-deoxy-β-D-lyxofuranosyl)胸苷。该申请还涉及这些化合物的制备方法以及将其用于合成3′-[18F]氟-3′-脱氧胸苷的用途。
• Synthesis of thymidine dimers containing piperazine in the internucleoside linkage and their incorporation into oligodeoxynucleotides
  作者：Gorm Vang Petersen、Jesper Wengel

  DOI：10.1016/0040-4020(94)01088-h

  日期：1995.2

  The synthesis of thymidine dimers in which the natural phosphodiester linkage has been replaced by piperazine (3′-(N(CH2CH2)2N)-5′, 9 and 3′-(N(CH2CH2)2N)-CO-4′, 10) are described. These new dimers were incorporated into oligodeoxynucleotides on an automated DNA-synthesizer using the phosphoramidite approach. The thermal stability of DNA/DNA duplexes and the enzymatic stability was studied by UV experiments

  胸苷二聚体的合成，其中天然磷酸二酯键已被哌嗪（3'-（N（CH 2 CH 2）2 N）-5'，9和3'-（N（CH 2 CH 2）2 N描述）-CO-4'，10）。使用亚磷酰胺方法，将这些新的二聚体掺入到自动DNA合成仪上的寡聚脱氧核苷酸中。通过UV实验研究了DNA / DNA双链体的热稳定性和酶促稳定性。用17聚体9掺入一次或在中间两次表现出热稳定性有显着降低（Δ Ť米〜-11℃下每修饰）而17聚体与10掺入一次或两次的中间仅表现出热稳定性稍微降低（Δ Ť米相比未修饰的17聚体时每修改〜-2δC）。此外，含有9或10的末端修饰的寡脱氧核苷酸显示出对蛇毒磷酸二酯酶的稳定性提高了五至六倍。
• A novel thiol protecting group: A 2-thioquinoline sulfide as a masked sulfhydryl moiety
  作者：Jiancun Zhang、Mark D. Matteucci

  DOI：10.1016/s0040-4039(98)02694-x

  日期：1999.2

  2-Thioquinoline sulfide was developed as a masked sulfhydryl entity. It is introduced through facile S(N)2 displacement reactions and is stable to a variety of reaction conditions including acids, bases and nucleophiles. It is readily unmasked using the mild treatment of sodium cyanoborohydride in acetic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.
• TT DINUCLEOTIDES CONTAINING AN ISOXAZOLINE MOIETY: SYNTHESIS AND BINDING AFFINITY STUDY
  作者：Jong Rock Kong、Sang Kook Kim、Byung Jo Moon、Su Jeong Kim、Byeang Hyean Kim

  DOI：10.1081/ncn-100107187

  日期：2001.12.31

  We have prepared four diastereomers of TT dinucleotides containing an isoxazoline moiety and four dodecanucleotides incorporating these TT dinucleotides in the middle of the DNA sequence. We also have determined the melting temperatures of these modified oligonucleotides (Tin values) by measuring change in UV absorbance.
• Incorporation of amide linked thymidine dimers into oligodeoxynucleotides
  作者：Garimella Viswanadham、Gorm V. Petersen、Jesper Wengel

  DOI：10.1016/0960-894x(96)00159-x

  日期：1996.4

  The synthesis of thymidine dimers in which the phosphodiester linkage has been replaced by an amide linkage containing diamines (homopiperazine, 2,5-trans-dimethylpiperazine, N,N-dimethylethylenediamine and N,N-diethylethylenediamine) and their incorporation into oligodeoxynucleotides is described. The thermal and nucleolytic stability of the resulting oligodeoxynucleotide analogues are reported. Copyright (C) 1996 Elsevier Science Ltd