1-(3,5-二甲氧基苯基)十七烷-1-醇 | 52482-84-5

• 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: 1-(3,5-二甲氧基苯基)十七烷-1-醇
• 英文名称: N⁴-acetyl-1-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)cytosine
• 英文别名: N⁴,O^2',O^5'-triacetyl-3'-bromo-3'-deoxycytidine；1-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)-N⁴-acetylcytosine；1-(2,5-Di-O-acetyl-3-bromo-3-desoxy-β-D-xylofuranosyl)-N⁴-acetylcytosin；4-acetylamino-1-(O²,O⁵-diacetyl-3-bromo-β-D-3-deoxy-xylofuranosyl)-1H-pyrimidin-2-one；N-[1-(2,5-Di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]acetamide；[(2R,3S,4S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-4-acetyloxy-3-bromooxolan-2-yl]methyl acetate
• CAS: 52482-84-5
• 化学式: C₁₅H₁₈BrN₃O₇
• 分子量: 432.228
• InChiKey: YPZSAHLCYHXMNE-YXCITZCRSA-N

物化性质

• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3,5-二甲氧基苯基)十七烷-1-醇 在 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 7.0h， 生成 3'-deoxy-3',4'-didehydrocytidine
  参考文献：
  名称：

  Allylic Substitution of 3‘,4‘-Unsaturated Nucleosides:  Organosilicon-Based Stereoselective Access to 4‘-C-Branched 2‘,3‘-Didehydro-2‘,3‘-dideoxyribonucleosides

  摘要：

  Reactions of organosilicon reagents (such as allyltrimethylsilane, silyl enol ethers, cyanotrimethylsilane) with 3',4'-unsaturated nucleosides (of uracil, N-4-acetylcytosine, and hypoxanthine) having an allyl ester structure were investigated in the presence of a Lewis acid in CH2Cl2. In the cases of uracil and N-4-acetylcytosine derivatives, SnCl4 appeared to be suitable, whereas the use of EtAlCl(2) was necessary for the hypoxanthine derivatives. The main pathway of these reactions was found to be a-face-selective S(N)2' allylic substitution, irrespective of the configuration of 2'-0-acyl leaving group. As a result, a new stereoselective operation for C-C bonds formation leading to 4'-carbon-substituted 2',3'-didehydro-2',3'-dideoxyribonucleosides has been disclosed for the first time. Stereochemistry of these 4'-C-branched products can be assigned on the basis of H-1 NMR spectroscopy in terms of the anisotropic shift of H-5 of the pyrimidine base (or H-8 of the hypoxanthine), which is caused by the 5'-0-(tert-butyldiphenylsilyl) protecting group.

  DOI：

  10.1021/jo9516190
• 作为产物：
  描述：

  胞苷 以 乙腈 为溶剂， 反应 4.0h， 生成 1-(3,5-二甲氧基苯基)十七烷-1-醇
  参考文献：
  名称：

  一种3’-脱氧尿苷的制备方法

  摘要：

  本发明涉及药物合成领域，具体是一种3’‑脱氧尿苷的制备方法，以化合物3为原料，先经乙酸酐保护氨基得到化合物4，再在乙酰溴作用下得到化合物5，经过次磷酸盐体系还原得到化合物6；在高压水蒸气与有机溶剂的作用下脱去脱乙酰氨基得化合物8或N‑乙酰基得化合物7，最后脱去全部乙酰基得到3’‑脱氧尿苷和3’‑脱氧胞苷的混合物，分离纯化分别得到3’‑脱氧尿苷和3’‑脱氧胞苷晶体；也可以由化合物6直接脱去全部乙酰基得到3’‑脱氧胞苷。本发明采用易得的天然产物为起始原料，操作简单，纯化方便，极易工业化大规模生产。

  公开号：

  CN107033205B

文献信息

• An Efficient and General Synthesis of 5′-Esters of 2′,3′-Didehydro-2′,3′-dideoxynucleosides: A Facile Opening of 2′,3′-Orthoacetates of Ribonucleosides Followed by Reductive Elimination of the Halogenoacetates
  作者：Ratnakar R. Talekar、Paul L. Coe、Richard T. Walker

  DOI：10.1055/s-1993-25853

  日期：——

  A three-step reaction sequence starting from a ribonucleoside to give the corresponding 5′-O-acyl-2′,3′-didehydro-2′,3′-dideoxynucleoside is described. The key intermediate is the bromoacetate, made by reaction of the 2′,3′-methoxyethylidene nucleoside with acetyl bromide. Reductive elimination of the bromoacetate using a zinc-copper couple furnishes the desired compounds in good overall yield.

  描述了一种从核糖核苷开始的三步反应序列，最终得到相应的5'-O-酰基-2',3'-二脱氧-2',3'-二氢核苷。关键中间体是溴乙酸酯，由2',3'-甲氧基亚乙基核苷与乙酰溴反应制得。利用锌-铜偶对溴乙酸酯进行还原消除，可在良好的总体产率下获得目标化合物。
• Modified nucleosides for the treatment of viral infections and abnormal cellular proliferation
  申请人：——

  公开号：US20030087873A1

  公开（公告）日：2003-05-08

  The disclosed invention is a composition for and a method of treating a Flaviviridae (including BVDV and HCV), Orthomyxoviridae (including Influenza A and B) or Paramyxoviridae (including RSV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans, using a nucleoside of general formula (I)-(XXIII) or its pharmaceutically acceptable salt or prodrug. This invention also provides an effective process to quantify the viral load, and in particular BVDV, HCV or West Nile Virus load, in a host, using real-time polymerase chain reaction (“RT-PCR”). Additionally, the invention discloses probe molecules that can fluoresce proportionally to the amount of virus present in a sample.

  该公开的发明涉及一种用于治疗Flaviviridae（包括BVDV和HCV）、Orthomyxoviridae（包括甲型和乙型流感）或Paramyxoviridae（包括RSV）感染或与异常细胞增殖有关的病况的组合物和方法，适用于宿主，包括动物，尤其是人类，使用通用式（I）-（XXIII）的核苷或其药学上可接受的盐或前药。该发明还提供了一种有效的过程，用于量化病毒载量，特别是BVDV、HCV或西尼罗河病毒载量，使用实时聚合酶链反应（RT-PCR）。此外，该发明揭示了可以与样本中存在的病毒数量成比例发光的探针分子。
• Nucleosides. III. Investigation of the Electrochemical Synthesis of N4, O5'-Diacetyl-2',3'-dideoxy-2',3'-didehydrocytidine
  作者：O Johansen、SM Marcuccio、AWH Mau

  DOI：10.1071/ch9941843

  日期：——

  The influence of the reaction conditions on the yield of N4,O5′-diacetyl-2′,3′-dideoxy-2′,3′-didehydrocytidine (3), by electrochemical synthesis from N4,O2′,O5′-triacetyl-3′-bromo-3′-deoxycytidine (2), has been studied in order to evaluate the potential of this reaction for synthesis on a larger scale. We have characterized the half-wave potentials of the precursor (2) and the product (3) by polarography under various conditions, and found that reduction in the base moiety can easily take place giving by-products. Furthermore, this reduction consumes protons leading to rapid solvolysis in protic solvents. We have demonstrated for the first time that (3) can be formed near quantitatively in both protic and aprotic solvents. The success of the synthesis of (3) as well as of other 2′,3′-dideoxy 2′,3′-didehydro nucleosides also depends to a large extent on how uniform the current density across the working electrode surface can be maintained during electrolysis.

  通过电化学合成 N4,O5′-二乙酰基-2′,3′-二脱氧-2′,3′-二脱氢胞苷 (3)，研究了反应条件对其产率的影响、O2′,O5′-三乙酰基-3′-溴-3′-脱氧胞苷（2）的电化学合成方法进行了研究，以评估该反应在更大规模合成方面的潜力。我们在各种条件下通过极谱法测定了前体（2）和产物（3）的半波电位，发现碱基很容易发生还原，从而产生副产物。此外，这种还原会消耗质子，导致在质子溶剂中迅速溶解。我们首次证明，(3) 可以在质子和非质子溶剂中近乎定量地生成。(3) 以及其他 2′,3′-二脱氧 2′,3′-二脱氢核苷的合成成功与否，在很大程度上还取决于电解过程中工作电极表面的电流密度是否均匀。
• 2′,3′－双脱氧胞苷的生产方法
  申请人：陆锦康

  公开号：CN1563030A

  公开（公告）日：2005-01-12

  本发明公开了一种2′，3′－双脱氧胞苷的生产方法，包括将胞苷与醋酐反应生成4－N－乙酰胞苷、进一步与溴化氢的饱和醋酸溶液在醋酐作为催化剂的条件下，反应生成溴代混合物、将溴代混合物在以锌铜偶为催化剂的条件下，反应生成4－N－乙酰－2＇，3＇－双脱氢－2＇，3＇－双脱氧胞苷5＇－乙酸酯、再进一步在Pd/C存在的条件下，进行加氢反应，生成4－N－乙酰－2′，3＇－双脱氧鸟苷5′－乙酸酯、然后在甲醇、三乙胺存在的条件下，反应生成2′，3′－双脱氧胞苷等步骤。本发明工艺简单，易操作，原料易得，产品得率高，达90％以上。
• Modified nucleosides for the treatment of viral infections and abnormal cellullar proliferation
  申请人：Stuyver Lieven

  公开号：US20110269707A1

  公开（公告）日：2011-11-03

  The disclosed invention is a composition for and a method of treating a Flaviviridae (including BVDV and HCV), Orthomyxoviridae (including Influenza A and B) or Paramyxoviridae (including RSV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans, using a nucleoside of general formula (I)-(XXIII) or its pharmaceutically acceptable salt or prodrug. This invention also provides an effective process to quantify the viral load, and in particular BVDV, HCV or West Nile Virus load, in a host, using real-time polymerase chain reaction (“RT-PCR”). Additionally, the invention discloses probe molecules that can fluoresce proportionally to the amount of virus present in a sample.

  本公开发明涉及一种用于治疗Flaviviridae（包括BVDV和HCV）、Orthomyxoviridae（包括甲型和乙型流感）或Paramyxoviridae（包括RSV）感染或与异常细胞增殖相关的条件的组合物和方法，适用于宿主，包括动物，特别是人类，使用通式（I）-（XXIII）的核苷或其药学上可接受的盐或前药。本发明还提供了一种有效的过程，用于定量病毒载量，特别是BVDV、HCV或西尼罗河病毒载量，在宿主中使用实时聚合酶链反应（“RT-PCR”）。此外，本发明还揭示了探针分子，可以与样品中存在的病毒数量成比例地发出荧光。