3’-O-乙酰基-2’-脱氧胞苷 | 72560-69-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 3’-O-乙酰基-2’-脱氧胞苷
• 中文别名: 3'-O-乙酰基-2'-脱氧胞苷
• 英文名称: 3'-O-acetyl-2'-deoxycytidine
• 英文别名: O^3'-acetyl-2'-deoxy-cytidine；O^3'-Acetyl-2'-desoxy-cytidin；[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] acetate
• CAS: 72560-69-1
• 化学式: C₁₁H₁₅N₃O₅
• mdl: MFCD00057458
• 分子量: 269.257
• InChiKey: ATBRMDNADDOXDD-QXFUBDJGSA-N

物化性质

• 沸点：
  459.4±55.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  3’-O-乙酰基-2’-脱氧胞苷 生成 [(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
  参考文献：
  名称：

  ZAXAROVA, L. YU.;ZUEVA, E. V., IZOTOPNOMECH. SOED. POLUCH., SVOJSTVA, METODY ANAL., L.,(1987) 16-18

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 在 吡啶 、 水 、 溶剂黄146 作用下， 生成 3’-O-乙酰基-2’-脱氧胞苷
  参考文献：
  名称：

  核苷酸。第二十三部分。衍生自脱氧胞苷的单核苷酸。注意胞苷酸a和b的结构

  摘要：

  DOI：

  10.1039/jr9540000034

文献信息

• A practical synthesis of nucleoside 5′-diphosphates from nucleoside 5′-<i>H</i>-phosphonate monoesters
  作者：Marta Rachwalak、Malgorzata Rozniewska、Justyna Golebiewska、Tomasz Jakubowski、Michal Sobkowski、Joanna Romanowska

  DOI：10.1080/00397911.2020.1814817

  日期：2020.12.16

  and convenient synthetic protocols based on H-phosphonate chemistry have been developed for the preparation of nucleoside 5′-diphosphates. It consists of oxidation of the silylated H-phosphonate monoesters in pyridine with iodine to produce the corresponding N-pyridiniumphosphonate intermediates, followed by their reactions with orthophosphoric acid used as a nucleophile. The added value of the method

  摘要 已经开发了一种基于 H-膦酸酯化学的简单方便的合成方案，用于制备核苷 5'-二磷酸。它包括在吡啶中用碘氧化甲硅烷基化的 H-膦酸酯单酯以产生相应的 N-吡啶鎓膦酸酯中间体，然后它们与用作亲核试剂的正磷酸反应。该方法的附加值是反应的底物 H-膦酸酯单酯可以由相应的核苷原位制备，无需分离即可用于下一步。该方法简单，适用于核糖和脱氧核糖核苷的各种二磷酸盐及其类似物的制备。图形概要
• A Versatile and Convenient Regioselective Acylation of 2′-Deoxynucleosides and Ribonucleosides by Supported Lipases of Pseudomonas Cepacia
  作者：Ranjeet V. Nair、Manikrao M. Salunkhe

  DOI：10.1080/00397910008086919

  日期：2000.9

  Abstract Pseudomonas Cepacia lipase supported on ceramic particles (lipase PS-C) and on diatomite (lipase PS-D) regioselectively acylated 2′-deoxynucleosides and ribonucleosides to 3′-O-acetyl-2′-deoxynucleosides and 3′-O-acetyl-ribonucleosides with oxime esters in organic solvents at room temperature. This enzymatic reaction was significant because the regioselectivity was total; as any other regioisomer

  摘要 洋葱假单胞菌脂肪酶负载在陶瓷颗粒（脂肪酶 PS-C）和硅藻土（脂肪酶 PS-D）上，将 2'-脱氧核苷和核糖核苷区域选择性酰化为 3'-O-乙酰基-2'-脱氧核苷和 3'-O-乙酰基-核糖核苷与肟酯在室温下在有机溶剂中。这种酶促反应很重要，因为区域选择性是完全的；观察到任何其他区域异构体和 N-酰化产物。
• Synthesis of α-P-Modified Nucleoside Diphosphates with Ethylenediamine
  作者：Ping Li、Zhihong Xu、Hongyan Liu、Charlotta K. Wennefors、Mikhail I. Dobrikov、János Ludwig、Barbara Ramsay Shaw

  DOI：10.1021/ja055179y

  日期：2005.12.1

  a one-pot synthesis of α-P-borano-, α-P-thio-, and α-P-seleno-modified nucleoside diphosphate analogues that are otherwise difficult to obtain. The key step involves the intramolecular nucleophilic attack by an amino group in 5 to remove the γ-phosphate. The absolute configurations of P-diastereomers were confirmed by analysis of their 1H NMR. Affinity studies revealed that the nucleoside boranodiphosphates

  本报告描述了 α-P-硼烷-、α-P-硫代-和 α-P-硒修饰的核苷二磷酸类似物的一锅合成，否则很难获得。关键步骤涉及 5 中的氨基进行分子内亲核攻击以去除 γ-磷酸盐。P-非对映异构体的绝对构型通过其 1H NMR 分析得到证实。亲和力研究表明，核苷硼二磷酸在抗病毒研究中可能有用。
• PROCEDE DE PREPARATION DE NUCLEOTIDES ET ANALOGUES A FAÇON PAR SYNTHESE SUR SUPPORT SOLUBLE ET OUTILS BIOLOGIQUES PREPARES
  申请人：Centre National de la Recherche Scientifique

  公开号：EP2265624A1

  公开（公告）日：2010-12-29
• METHOD FOR PREPARING NUCLEOTIDES AND RELATED ANALOGUES BY SYNTHESIS ON SOLUBLE SUBSTRATE, AND BIOLOGICAL TOOLS THUS PREPARED
  申请人：Peyrottes Suzanne

  公开号：US20110118454A1

  公开（公告）日：2011-05-19

  The invention concerns a method for preparing monomer nucleotides or nucleotide analogues comprising the steps of: (1) coupling a soluble polyethylene glycol support provided with at least one diacid or ether-acid linker and a monomer nucleoside or nucleoside analogue to an amine group or hydroxyl group of the nucleoside with the aid of a coupling agent; (2) at least one step for phosphorylation of said nucleoside or nucleoside analogue coupled to said support with a phosphorylation agent; (3) cleavage of said support and recovery of at least one monomer nucleotide or nucleotide analogue. The nucleotides prepared are biological tools.