O^5'-tert-butyldimethylsilyl-N⁶,N⁶,O^2',O^3'-tetrabenzoyladenosine | 1031809-76-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: O^5'-tert-butyldimethylsilyl-N⁶,N⁶,O^2',O^3'-tetrabenzoyladenosine
• 英文别名: [(2R,3R,4R,5R)-4-benzoyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-[6-(dibenzoylamino)purin-9-yl]oxolan-3-yl] benzoate
• CAS: 1031809-76-3
• 化学式: C₄₄H₄₃N₅O₈Si
• 分子量: 797.94
• InChiKey: VCCDUSMZHHZENV-WCMBYXODSA-N

物化性质

• 熔点：
  159-160 °C
• 沸点：
  857.8±75.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.68
• 重原子数：
  58
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  O^5'-tert-butyldimethylsilyl-N⁶,N⁶,O^2',O^3'-tetrabenzoyladenosine 在 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以99 %的产率得到N6-二苯甲酰基腺苷-2',3'-二苯甲酸酯
  参考文献：
  名称：

  SuFEx 实现的醇的直接脱氧多样化

  摘要：

  我们介绍了磺酰氟作为双功能试剂的一种新用途，可促进复杂醇库的一步脱氧多样化。我们的反应设计采用硫 (VI) 氟化物交换 (SuFEx) 介导的醇活化和氟化物诱导的硅结合亲核试剂活化。该方法能够通过 C-C、C-N、C-Cl 和 C-Br 键的形成将复杂分子中的醇 C-O 键直接转化为不同的类似物，同时抑制任何消除副产物。

  DOI：

  10.1021/acs.orglett.4c01016
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 O^5'-tert-butyldimethylsilyl-N⁶,N⁶,O^2',O^3'-tetrabenzoyladenosine
  参考文献：
  名称：

  Design and Synthesis of α-Carboxy Phosphononucleosides

  摘要：

  Rhodium catalyzed O-H insertion reactions employing alpha-diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5'-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an alpha-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.

  DOI：

  10.1021/jo101738e

文献信息

• Novel Synthetic Approach to Multibenzoylated Nucleosides
  作者：Xue‐Feng Zhu、A. Ian Scott

  DOI：10.1080/00397910801916280

  日期：2008.4

  Abstract An improved and highly efficient synthetic approach to multibenzoylated nucleosides bearing free 5′‐hydroxyl groups is described here. By employing t-butyldimethylsilyl (TBDMS) rather than the more commonly used dimethoxytrityl (DMTr) as a temporary 5′‐OH protecting group of the starting nucleoside, this methodology provides the expected products in nearly quantitative yields, thereby substantially

  摘要 这里描述了一种改进的、高效的带有游离 5'-羟基的多苯甲酰化核苷的合成方法。通过使用叔丁基二甲基甲硅烷基 (TBDMS) 而不是更常用的二甲氧基三苯甲基 (DMTr) 作为起始核苷的临时 5'-OH 保护基团，该方法以接近定量的产率提供了预期的产品，从而大大降低了成本和工作量的合成。
• Deprotection of silyl ethers by using SO3H silica gel: Application to sugar, nucleoside, and alkaloid derivatives
  作者：Hideaki Fujii、Naoyuki Shimada、Masaki Ohtawa、Fumika Karaki、Masayoshi Koshizuka、Kohei Hayashida、Mitsuhiro Kamimura、Kazuishi Makino、Tohru Nagamitsu、Hiroshi Nagase

  DOI：10.1016/j.tet.2017.07.047

  日期：2017.9

  silylated sugar, nucleoside, and alkaloid derivatives. The treatment with SO3H silica gel provided desilylated products in good to excellent yield. In the reactions of sugar and nucleoside derivatives, no silyl residue was detected in the crude products, but the crude products of the reaction of alkaloids contained small amounts of silyl residues. Even though the sugar and nucleoside derivatives had a

  我们使用甲硅烷基化糖，核苷和生物碱衍生物，使用经烷基磺酸基团修饰的表面的SO 3 H硅胶进行脱甲硅烷基化反应。用SO 3 H硅胶处理可以很好地获得优良的收率的甲硅烷基化产物。在糖和核苷衍生物的反应中，在粗产物中未检测到甲硅烷基残基，但是生物碱反应的粗产物中含有少量甲硅烷基残基。即使糖和核苷衍生物分别具有不稳定的糖基和C N键，这些键仍可耐受反应条件。这些结果表明，使用SO 3进行去甲硅烷基化的程序H硅胶将适用于各种类型的被甲硅烷基保护的化合物的脱保护。在克规模的实验中，脱甲硅烷基化过程成功进行，而未观察到粗产物中的任何甲硅烷基残基。
• Preparation of fluorinated RNA nucleotide analogs potentially stable to enzymatic hydrolysis in RNA and DNA polymerase assays
  作者：Anton Shakhmin、John-Paul Jones、Inessa Bychinskaya、Mikhail Zibinsky、Keriann Oertell、Myron F. Goodman、G.K. Surya Prakash

  DOI：10.1016/j.jfluchem.2014.07.019

  日期：2014.11

  Analogs of ribonucleotides (RNA) stable to enzymatic hydrolysis were prepared and characterized. Computational investigations revealed that this class of compounds with a modified triphosphate exhibits the correct polarity and minimal steric effects compared to the natural molecule. Non-hydrolysable properties as well as the ability of the modified nucleotide to be recognized by enzymes were probed by performing single-turnover gap filling assays with T7 RNA polymerase and DNA polymerase beta. (C) 2014 Elsevier B.V. All rights reserved.
• Design and Synthesis of α-Carboxy Phosphononucleosides
  作者：Sebastien Debarge、Jan Balzarini、Anita R. Maguire

  DOI：10.1021/jo101738e

  日期：2011.1.7

  Rhodium catalyzed O-H insertion reactions employing alpha-diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5'-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an alpha-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.
• 10.1021/acs.orglett.4c01016
  作者：Odoh, Amaechi Shedrack、Keeler, Courtney、Kim, Byoungmoo

  DOI：10.1021/acs.orglett.4c01016

  日期：——

  We introduce a new use of sulfonyl fluoride as a bifunctional reagent that facilitates the one-step deoxy-diversification of complex alcohol libraries. Our reaction design features a Sulfur(VI) Fluoride Exchange (SuFEx) mediated activation of alcohols and fluoride-induced activation of silicon-bound nucleophiles. This method enables the direct conversion of alcoholic C–O bonds in complex molecules into

  我们介绍了磺酰氟作为双功能试剂的一种新用途，可促进复杂醇库的一步脱氧多样化。我们的反应设计采用硫 (VI) 氟化物交换 (SuFEx) 介导的醇活化和氟化物诱导的硅结合亲核试剂活化。该方法能够通过 C-C、C-N、C-Cl 和 C-Br 键的形成将复杂分子中的醇 C-O 键直接转化为不同的类似物，同时抑制任何消除副产物。