2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine | 70838-44-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine
• 英文别名: 5'-O-benzoyl-2,3'-anhydro-3'-deoxthymidine；2,3'-Anhydro-5'-O-benzoylthymidine；5'-O-benzoyl-2,3'-anhydrothymidine；5-O-benzoyl-2,3'-anhydrothymidine；[(1R,9R,10R)-4-methyl-5-oxo-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-10-yl]methyl benzoate
• CAS: 70838-44-7
• 化学式: C₁₇H₁₆N₂O₅
• mdl: MFCD01332880
• 分子量: 328.324
• InChiKey: WUQUVOAMQGVMKB-MGPQQGTHSA-N

物化性质

• 熔点：
  230-235°C (dec.)
• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine 在 双氧水 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 司他夫定
  参考文献：
  名称：

  Efficient Transformation of Thymidine into 2′,3′-Didehydro-2′,3′-Dideoxy-Thymidine (D4T) Involving Opening of a 2,3′-Anhydro Derivative by Phenylselenol

  摘要：

  A new, high-yielding method for introduction of the selenophenyl residue at the 3'- position of thymidine is reported. This reaction avoided any strongly basic or reductive reagent, thus allowing the use of benzoate ester as a protective group at O-5'. Further oxidation-elimination sequence followed by basic deprotection afforded 2',3'-didehydro-2',3'-dideoxythymidine (D4T) in 67.5 % overall yield from thymidine.

  DOI：

  10.1080/15257779508010686
• 作为产物：
  描述：

  ((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(methylsulfonyloxy)-tetrahydrofuran-2-yl)methyl benzoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 丙酮 为溶剂， 生成 2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine
  参考文献：
  名称：

  由5-甲基尿苷合成抗艾滋病药物AZT的新方法

  摘要：

  The anti-AIDS drug AZT is prepared in six steps in 44% overall yield starting from the readily available ribonucleoside 5-methyluridine.

  DOI：

  10.1016/0040-4039(95)01753-5

文献信息

• One-step conversion of thymidine into 2,3′-anhydro derivatives
  作者：Stanislas Czernecki、Jean-Marc Valery

  DOI：10.1039/c39900000801

  日期：——

  2,3′-Anhydro derivatives of thymidine are obtained in ca. 80% yield by a one-pot transformation involving a tandem Mitsunobu reaction.

  大约在2,3'中获得了胸苷的2,3'-脱水衍生物。通过一锅转化（包括串联的Mitsunobu反应）可达到80％的收率。
• Synthesis of 3‘- and 5‘-Nitrooxy Pyrimidine Nucleoside Nitrate Esters:  “Nitric Oxide Donor” Agents for Evaluation as Anticancer and Antiviral Agents
  作者：Ebrahim Naimi、Aihua Zhou、Panteha Khalili、Leonard I. Wiebe、Jan Balzarini、Erik De Clercq、Edward E. Knaus

  DOI：10.1021/jm020299r

  日期：2003.3.1

  lines possessing the herpes simplex virus type 1 (HSV-1) thymidine kinase gene (TK(+)) were observed, indicating that expression of the viral TK enzyme did not provide a gene therapeutic effect. These nitrate esters were inactive antiviral agents except for 5-iodo-3'-O-nitro-2'-deoxyuridine that showed modest activity against HSV-1, HSV-2, and vaccinia virus.

  一组3'-O-硝基-2'-脱氧尿苷，3'-O-硝基-2'-脱氧胞苷和5'-O-硝基-2'-脱氧尿苷具有各种取代基（H，Me，F ，I）在C-5位被合成为具有抗癌/抗病毒剂的能力，所述抗癌/抗病毒剂具有伴随释放细胞毒性一氧化氮（* NO）的能力。尽管这些化合物通常在l-半胱氨酸或血清存在下孵育后释放的NO含量比参考药物异山梨醇二硝酸盐更高，但它们的细胞毒性（CC（50）= 10（-3）至10（-6）M范围）与5-碘-2'-脱氧尿苷相当，但对多种癌细胞系却比5-氟-2'-脱氧尿苷弱。对未转染的（KBALB，143B）和相应的转染的（KBALB-STK，观察到具有1型单纯疱疹病毒（HSV-1）胸苷激酶基因（TK（+））的143B-LTK）癌细胞系，表明病毒TK酶的表达未提供基因治疗作用。这些硝酸酯是无活性的抗病毒药，除了5-碘-3'-O-硝基-2'-脱氧尿苷对HSV-1，HSV-2和牛痘病毒表现出适度的活性。
• 2‘,3‘-Dideoxy-3‘-thionucleoside Triphosphates:  Syntheses and Polymerase Substrate Activities
  作者：Meena、Mui Sam、Kathryn Pierce、Jack W. Szostak、Larry W. McLaughlin

  DOI：10.1021/ol070147w

  日期：2007.3.1

  All four 2',3'-dideoxy-3'-thio-nucleosides (ddtNTPs) function as substrates for the Y410F mutant of Deep Vent (exo-) DNA polymerase. Not only are the ddtNTPs incorporated to form the N + 1 product, but further elongations are observed in which the key step is attack of the 3'-thiol on the 5'-triphosphate. Although other polymerases are likely to differ in their use of the ddtNTPs, there does not appear

  所有四个2'，3'-dideoxy-3'-thio-nucleosides（ddtNTPs）充当Deep VeNT（exo-）DNA聚合酶Y410F突变体的底物。不仅掺入了ddtNTP以形成N + 1产物，而且还观察到了进一步的延伸，其中的关键步骤是3'-硫醇对5'-三磷酸的侵蚀。尽管其他聚合酶在ddtNTPs的使用上可能会有所不同，但似乎没有根本禁止在磷酸酐亲电试剂上使用硫醇亲核试剂的方法。描述了四个ddtNTP（C，T，A，G）的合成。[结构：见文字]
• Synthesis of tritium-labelled 3?-azido-3?-deoxythymidine
  作者：G.V. Sidorov、Yu.B. Zverkov、N.F. Myasoedov、M.V. Jasko、Yu.S. Skoblov

  DOI：10.1002/jlcr.707

  日期：2003.6

  approaches to the synthesis of 3′-azido-3′-deoxythymidine labelled with tritium in the heterocyclic base have been developed. With this aim, enzymatic transribosylation with [3H]thymine using the enzyme preparation from rat liver and a three-step chemical synthesis with use of the tritium labelled precursor were studies. The enzyme preparation did not catalyse the transfer of the 3′-azido-3′-deoxyribosyl

  已经开发了合成在杂环碱基中用氚标记的 3'-azido-3'-deoxythymidine 的新方法。为此，研究了使用来自大鼠肝脏的酶制剂与 [3H] 胸腺嘧啶的酶促转核糖基化以及使用氚标记的前体进行的三步化学合成。酶制剂不催化 3'-叠氮基-3'-脱氧核糖基片段向 [3H] 胸腺嘧啶残基的转移。5'-O-Benzoyl-2,3'-anhydrothymidine 作为化学方法标记氚的前体。得到的[3H]3'-叠氮基-3'-脱氧胸苷的比放射性为18.3 Ci/mmol，氚位于胸腺嘧啶残基的C-6位。版权所有 © 2003 John Wiley & Sons, Ltd.
• Athermal, Chemically Triggered Release of RNA from Thioester Nucleic Acids
  作者：Sudheendran Mavila、Heidi R. Culver、Alex J. Anderson、Tania R. Prieto、Christopher N. Bowman

  DOI：10.1002/anie.202110741

  日期：2022.1.3

  Thioester linked oligo(T) nucleic acids are utilized for an efficient enrichment of mRNA from total RNA under ambient temperature. The selective binding of uncharged oT TENA to the poly(A) tail of the mRNA and release via a self-immolative degradation of thioester backbone under ambient temperature were the key features that enabled this approach.

  硫酯连接的寡 (T) 核酸用于在环境温度下从总 RNA 中有效富集 mRNA。不带电的 oT TENA 与 mRNA 的 poly(A) 尾的选择性结合，并在环境温度下通过硫酯骨架的自我牺牲降解释放是实现这种方法的关键特征。