5',N4-dibenzoyldeoxycytidine | 4803-92-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5',N4-dibenzoyldeoxycytidine
• 英文别名: (5'-O,4-N)-dibenzoyl-2'-deoxycytidine；N-Benzoyl-2'-deoxy-cytidin-5'-benzoat；N4,5'-O-dibenzoyl-2'-deoxycytidine；N⁴,O^5'-dibenzoyl-2'-deoxy-cytidine；N-Benzoyl-5'-O-benzoyl-2'-deoxycytidine；[(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 4803-92-3
• 化学式: C₂₃H₂₁N₃O₆
• 分子量: 435.436
• InChiKey: ADBLMNPUSHTBKL-NLWGTHIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5',N4-dibenzoyldeoxycytidine 在 三氟化硼乙醚 三氟甲磺酸 、 phosphorus pentoxide 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 3.5h， 生成 Cytidine, 3'-O-[(acetyloxy)methyl]-N-benzoyl-2'-deoxy-, 5'-benzoate
  参考文献：
  名称：

  合成（3'→5'）亚甲基缩醛连接的二核苷的另一种方法

  摘要：

  使用三甲基甲硅烷基三氟甲磺酸酯（5a-c）将5'-O-乙酰丙酰基-3'-O-苯甲酰氧基甲基胸苷或5'-O-苯甲酰基-3'-O-乙酰氧基甲基胸苷与适当保护的胸苷，d-胞苷或d-鸟苷受体5a–c缩合（ TMSOTf）作为活化系统，提供了各自的（3'→5'）亚甲基缩醛连接的二聚体d（T∧T），d（T∧G）。同样，TMSOtf促进的（5'-O，4-N）二苯甲酰基-3'-O-乙酰氧基甲基-2'-脱氧胞苷与受体5a–c的缩合产生相应的d（C∧T），d（C∧C ）和d（C∧G）二聚体。

  DOI：

  10.1016/s0040-4039(00)79605-5
• 作为产物：
  描述：

  N-苯甲酰-2'-脱氧胞苷 生成 5',N4-dibenzoyldeoxycytidine
  参考文献：
  名称：

  LIGUORI, ANGELO;PERRI, ENZO;SINDONA, GIOVANNI;UCCELLA, NICOLA, TETRAHEDRON, 44,(1988) N 1, 229-234

  摘要：

  DOI：

文献信息

• Novel Chemoenzymatic Protocol for the Synthesis of 3‘-<i>O</i>-Dimethoxytrityl-2‘-deoxynucleoside Derivatives as Building Blocks for Oligonucleotide Synthesis
  作者：Alba Díaz-Rodríguez、Susana Fernández、Yogesh S. Sanghvi、Miguel Ferrero、Vicente Gotor

  DOI：10.1021/op050253i

  日期：2006.5.1

  An easy, efficient, and scalable chemoenzymatic strategy for the synthesis of 3‘-O-dimethoxytrityl-2‘-deoxynucleosides has been developed. A key feature of this approach is the regioselective synthesis of 5‘-O-levulinyl-2‘-deoxynucleosides through enzymatic acylation in the presence of Candida antarctica lipase B. In addition, it was observed that the deblocking of levulinyl group from the 5‘-position

  已经开发了用于合成3' - O-二甲氧基三苯甲基-2'-脱氧核苷的简单，有效且可扩展的化学酶策略。该方法的关键特征是在南极假丝酵母脂肪酶B存在下，通过酶促酰化反应进行5'- O-乙酰丙氨酰-2'-脱氧核苷的区域选择性合成。此外，还观察到乙酰丙氨酰基从5'解封位置与常规的碱保护基完全相容。为了证明该方法的可扩展性，以25 g规模合成了3'- O-二甲氧基三苯甲基胸苷（4a）。这些单体（4 a - d）是合成寡核苷酸的有用组成部分。
• Synthesis and p-diastereomeric resolution of nucleoside 3′-O(s-alkyl) and nucleoside 3′-O(s-aryl) methylphosphonothioates
  作者：Wolfgang K.-D. Brill、Marvin H. Caruthers

  DOI：10.1016/s0040-4039(00)80262-2

  日期：1988.1

  Successive displacement of oxybenzotriazoyl moieties from methylphosphonicbisoxybenzotriazolide by a deoxynucleoside and a mercaptan yields the O,S-dialkyl and O-alkyl-S-arylmethylphosphonothioate diastereomers which can be resolved by flash column chromatography.

  通过脱氧核苷和硫醇从甲基膦酸双氧基苯并三唑基上连续取代氧基苯并三唑基部分，得到O，S-二烷基和O-烷基-S-芳基甲基硫代膦酸酯非对映异构体，可以通过快速柱色谱法拆分。
• Chemoenzymatic Synthesis of 3′-<i>O</i>-Acetal-Protected 2′-Deoxynucleosides as Building Blocks for Nucleic Acid Chemistry
  作者：Tatiana Rodríguez-Pérez、Susana Fernández、Saúl Martínez-Montero、Tania González-García、Yogesh S. Sanghvi、Vicente Gotor、Miguel Ferrero

  DOI：10.1002/ejoc.200901428

  日期：2010.3

  , and tetrahydrofuranyl ethers of 2'-deoxynucleosides, which are useful building blocks for nucleic acid chemistry. Enzymatic benzoylation provides an efficient alternative for protecting the 5'-hydroxy group of the parent nucleosides in a regioselective manner. Subsequently, tetra-hydropyranylation and tetrahydrofuranylation of the 2'-deoxynucleosides at the 3'-hydroxy group were accomplished with

  我们开发了一种简单方便的合成策略，用于制备 2'-脱氧核苷的四氢吡喃基、4-甲氧基-四氢吡喃基和四氢呋喃基醚，它们是核酸化学的有用组成部分。酶促苯甲酰化为以区域选择性方式保护母体核苷的 5'-羟基提供了一种有效的替代方法。随后，以对甲苯磺酸、MgBr 2 或樟脑磺酸为催化剂，对3'-羟基上的2'-脱氧核苷进行四氢吡喃化和四氢呋喃化反应。5'-O-苯甲酰基的脱保护提供了 3'-O-缩醛保护的 2'-脱氧核苷。三步法有望实现受保护核苷的大规模合成。
• Chemo and regioselective acylation of deoxyribonucleosides by means op n,n-bis-(2-oxo-oxazolidin-3-yl) phosphorodiammidic chloride (bopdc)
  作者：Angelo Liguori、Enzo Perri、Giovanni Sindona、Nicola Uccela

  DOI：10.1016/s0040-4020(01)85111-5

  日期：1988.1

  can be obtained by direct acylation of the substrates with carboxylic acid after activation with N,N-bis-(2-oxo-oxazolidin-3-yl) phosphorodiammidic chloride (BOPDC). In the same experimental conditions a chemoselective benzoylation of unprotected deoxyadenosine can be carried out. Nucleotide building blocks have been prepared from the base labile 5 '-protected nucleosides thus obtained.

  在N，N-双-（2-氧代-恶唑烷-3-基）磷二酰胺基氯化物（BOPDC）活化后，通过用羧酸直接将底物酰化，可获得高产率的5'-酰基-脱氧核糖核苷。在相同的实验条件下，可以进行未保护的脱氧腺苷的化学选择性苯甲酰化。已经从由此获得的碱基不稳定的5'-保护的核苷制备了核苷酸构件。
• A mild, efficient and regioselective enzymatic procedure for 5′-O-benzoylation of 2′-deoxynucleosides
  作者：Javier Garcı́a、Susana Fernández、Miguel Ferrero、Yogesh S. Sanghvi、Vicente Gotor

  DOI：10.1016/j.tetlet.2003.12.098

  日期：2004.2

  Lipase from Candida antarctica B catalyzes the selective monobenzoylation at the 5'-hydroxyl group of 2'-deoxynucleosides using vinyl benzoate as acyl transfer reagent in quantitative yields. The industrial suitability of this process via the reclaim and reuse of enzyme and vinyl benzoate has been demonstrated. (C) 2003 Elsevier Ltd. All rights reserved.