1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine | 42214-24-4

• 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-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine
• 英文别名: 3'-O-(methylsulfonyl)-5'-O-trityl-2'-deoxythymidine；5′-O-trityl-3′-O-mesylthymidine；5'-O-tritylthimidine 3'-methanesulfonate；5'-trityl-3'-methanesulfonylthymidine；3'-O-mesyl-5'-O-tritylthymidine；O^3'-methanesulfonyl-O^5'-trityl-thymidine；[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(trityloxymethyl)oxolan-3-yl] methanesulfonate
• CAS: 42214-24-4
• 化学式: C₃₀H₃₀N₂O₇S
• 分子量: 562.643
• InChiKey: NLAIOTWSOVURMN-OYUWMTPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine 在 lithium aluminium tetrahydride 、 双氧水 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 生成 司他夫定
  参考文献：
  名称：

  Selenium nucleophiles for the preparation of antiviral nucleosides

  摘要：

  The reactivity of nucleophilic selenium species toward nucleoside derivatives has been examined. A number of new 2'-deoxyribose nucleosides have been synthesized using this methodology. The cis elimination of the selenoxide obtained from the oxidation of the corresponding phenylselenide has been shown to be an efficient method for the preparation of the 2',3'-unsaturated antiviral nucleoside 1-(2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine (DAT).

  DOI：

  10.1021/jo00006a037
• 作为产物：
  描述：

  2-溴-2-脱氧-5-甲基脲啶-3,5-二乙酸酯 在 吡啶 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine
  参考文献：
  名称：

  制备齐多夫定及其中间体的方法

  摘要：

  一种制备齐多夫定（B）的方法，所述方法包括如下步骤：1）以2’-卤代胸苷（A）为原料，将其5’-位羟基进行保护，得到式（I）化合物；2）式（I）化合物经3’-位羟基酰化得到式（VI）化合物；3）式（VI）化合物经脱卤得到式(III)化合物；4）式（III）化合物消除得到式(IV)化合物,5）式（IV）化合物经叠氮化反应得到式（V）化合物；6）式（V）化合物脱保护得到齐多夫定（B）;具体的反应式如下（C）。式中：X为卤素；P1为羟基保护基；P2为C1-4烷基磺酰基、氟代的C1-4烷基磺酰基、芳基磺酰基或-CS-R，其中R为C1-4烷基。

  公开号：

  CN103443095B

文献信息

• Synthesis and Anti-HIV Activity of Triazolo-Fused 3′,5′-Cyclic Nucleoside Analogues Derived from an Intramolecular Huisgen 1,3-Dipolar Cycloaddition
  作者：Jingbo Sun、Xinyu Liu、Hongming Li、Ronghui Duan、Jinchang Wu

  DOI：10.1002/hlca.201100366

  日期：2012.5

  Triazolo‐fused 3′,5′‐cyclic nucleoside analogues were synthesized by an intramolecular 1,3‐dipolar cycloaddition of nucleoside‐derived azido‐alkynes in a regio‐ and stereospecific manner. The thymine nucleoside base in these target compounds was transformed successfully into the corresponding 5‐methylcytosine component. The synthesized compounds were examined in a MAGI assay for exploring the anti‐HIV

  Triazolo融合的3'，5'-环核苷类似物是通过核苷衍生的叠氮炔的分子内1,3-偶极环加成以区域和立体特异性方式合成的。这些目标化合物中的胸腺嘧啶核苷碱基已成功转化为相应的5-甲基胞嘧啶成分。在MAGI分析中检查了合成的化合物，以探索抗HIV活性；在H9 T淋巴细胞分析中，检查了化合物的细胞毒性。
• Antiviral Activity of Various 1-(2′-Deoxy-β-<scp>d</scp>-lyxofuranosyl), 1-(2′-Fluoro-β-<scp>d</scp>-xylofuranosyl), 1-(3′-Fluoro-β-<scp>d</scp>-arabinofuranosyl), and 2′-Fluoro-2′,3′-didehydro-2′,3′-dideoxyribose Pyrimidine Nucleoside Analogues against Duck Hepatitis B Virus (DHBV) and Human Hepatitis B Virus (HBV) Replication
  作者：Naveen C. Srivastav、Neeraj Shakya、Michelle Mak、Babita Agrawal、D. Lorne Tyrrell、Rakesh Kumar

  DOI：10.1021/jm100803c

  日期：2010.10.14

  3′-fluoroarabinofuranosyl, and 2′-fluoro-2′,3′-didehydro-2′,3′-dideoxyribose pyrimidine nucleoside analogues for antiviral activities against hepatitis B virus. Among the compounds examined, 1-(2-deoxy-β-d-lyxofuranosyl)thymine (23), 1-(2-deoxy-β-d-lyxofuranosyl)-5-trifluoromethyluracil (25), 1-(2-deoxy-2-fluoro-β-d-xylofuranosyl)uracil (38), 1-(2-deoxy-2-fluoro-β-d-xylofuranosyl)thymine (39), 2′,3′-dideoxy-2′,3′-d

  尽管存在成功的疫苗和抗病毒疗法，但乙型肝炎病毒（HBV）的感染仍然是急性和慢性肝病以及高死亡率的全球主要原因。我们合成并评估了几种lyxofuranosyl，2'-fluorooxylofuranosyl，3'-fluoroarabinofuranosyl和2'-fluoro-2'，3'-didehydro-2'，3'-dideoxyribose嘧啶核苷类似物对乙型肝炎病毒的抗病毒活性。在所检查的化合物中，1-（2-脱氧-β - d-呋喃呋喃糖基）胸腺嘧啶（23），1-（2-脱氧-β - d-呋喃呋喃糖基）-5-三氟甲基尿嘧啶（25），1-（2-脱氧-2-氟-β - d-木呋喃糖基）尿嘧啶（38），1-（2-脱氧-2-氟-β- d-二呋喃呋喃糖基）胸腺嘧啶（39），2'，3'-二脱氧-2'，3'-二脱氢-2'-氟胸苷（48）和2'，3'-二脱氧-2'，3'-二脱氢-2在原代鸭肝细胞中发现'
• Uracil- and thymine-substituted thymidine and uridine derivatives
  作者：Anna M. Costa、Montserrat Faja、Jaume Farràs、Jaume Vilarrasa

  DOI：10.1016/s0040-4039(98)00100-2

  日期：1998.3

  The four possible 3′-uracil-1-yl and 3′-thymin-1-yl derivatives of 3′-deoxythymidine and the four analogous derivatives of 2′-deoxyuridine have been synthesised from thymidine and uridine, respectively. Advantages of the 2-(methoxycarbonyl)vinyl group to prevent the formation of anhydronucleosides and of SnCl2/PhSH/Et3N in relation to H2/Pd for the reduction of most azido groups are disclosed.

  3'-脱氧胸苷的四种可能的3'-尿嘧啶-1-基和3'-胸腺嘧啶-1-基衍生物以及2'-脱氧尿苷的四种类似衍生物已分别从胸苷和尿苷合成。公开了相对于H 2 / Pd，2-（甲氧基羰基）乙烯基防止H 2 / Pd形成脱水核苷的优点和SnCl 2 / PhSH / Et 3 N减少大多数叠氮基的优点。
• Method for sequencing DNA and RNA by synthesis
  申请人：——

  公开号：US07544794B1

  公开（公告）日：2009-06-09

  This invention relates to the field of nucleic acid chemistry, more specifically to the field of compositions and processes that are nucleic acid analogs. More specifically, this invention relates to compositions that allow the sequencing of oligonucleotides by synthesis, and processes for sequencing by synthesis that exploit these compositions. Most specifically, the instant invention discloses compositions of matter that are 5′-triphosphates of ribo- and 2′-deoxyribonucleosides wherein the 3′-OH group is replaced by a 3′-ONHR group in the alpha configuration, wherein R is either a H or CH3 group. Also disclosed are these triphosphates where the nucleobase carries, via a linker, a reporter groups, such as a fluorescent species that can be used in single- or multi-copy DNA sequencing, or a tag that can be visualized by ultramicroscopy. Also disclosed are processes that use these compositions to do sequencing by synthesis.

  这项发明涉及核酸化学领域，更具体地涉及核酸类似物的组合物和过程领域。更具体地说，这项发明涉及一种允许通过合成测序寡核苷酸的组合物，以及利用这些组合物进行合成测序的过程。最具体地，本发明揭示了一种物质组合物，其中为核糖核苷酸和2'-脱氧核糖核苷酸的5'-三磷酸，其中3'-OH基团被3'-ONHR基团取代，且R为H或CH3基团。还公开了这些三磷酸，其中核碱基通过连接物携带报告基团，例如可用于单拷贝或多拷贝DNA测序的荧光物种，或者可通过超微显微镜可视化的标签。还公开了利用这些组合物进行合成测序的过程。
• Optimized synthesis of 3′-<i>O</i>-aminothymidine and evaluation of its oxime derivative as an anti-HIV agent
  作者：Pavel N. Solyev、Maxim V. Jasko、Tatiana A. Martynova、Ludmila B. Kalnina、Dmitry N. Nosik、Marina K. Kukhanova

  DOI：10.1515/hc-2015-0150

  日期：2015.10.1

  The synthesis and isolation of 3′-O-aminothymidine oximes have been optimized. Synthesized compounds were characterized by NMR and UV spectral and analytical data. A mixture of previously not reported syn and anti isomers of acetaldoximes was assessed for anti-HIV activity and the prevention of syncytia formation caused by HIV-1 infection.

  摘要：优化了3'-氨基胸苷肟的合成和分离。合成的化合物通过核磁共振和紫外光谱以及分析数据进行了表征。对以前未报道的乙醛肟的syn和anti异构体混合物进行了评估，以了解其抗HIV活性和预防HIV-1感染引起的合胞体形成。