1-(2',3'-O-isopropylidene-5',6'-dideoxy-6',6'-dibromo-β-D-ribo-5'-hexenofuranosyl)uracil | 64189-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(2',3'-O-isopropylidene-5',6'-dideoxy-6',6'-dibromo-β-D-ribo-5'-hexenofuranosyl)uracil
• 英文别名: 1-(5,6-dideoxy-6,6-dibromo-2,3-O-isopropylidene-β-D-enofuranosyl)pyrimidine-2,4(1H-3H)-dione；1-(6,6-dibromo-O²,O³-isopropylidene-β-D-ribo-5,6-dideoxy-hex-5-enofuranosyl)-1H-pyrimidine-2,4-dione；1-[(3aR,4R,6R,6aR)-6-(2,2-dibromoethenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4-dione
• CAS: 64189-19-1
• 化学式: C₁₃H₁₄Br₂N₂O₅
• 分子量: 438.073
• InChiKey: GGHBSKMWUPAUBE-FOBYXSAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2',3'-O-isopropylidene-5',6'-dideoxy-6',6'-dibromo-β-D-ribo-5'-hexenofuranosyl)uracil 在 吡啶 、 正丁基锂 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 水 、 丙酮 为溶剂， 反应 23.5h， 生成 1-(5-ethynylfuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of 3′-azido-4′-ethynyl-3′,5′-dideoxy-5′-norarabinouridine: a new anti-HIV nucleoside analogue

  摘要：

  3'-Azido-4'-ethynyl-3',5'dideoxy-5'-norarabinouridine 10 was synthesized from commercial uridine 1 in which the key step is the opening of protected 2',3'-epoxyuridine derivative 7 by sodium azide and the hydroxymethyl at 4-position of the ribose ring are replaced by ethynyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.054
• 作为产物：
  描述：

  (3aS,4S,6R,6aR)-6-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以2.25 g的产率得到1-(2',3'-O-isopropylidene-5',6'-dideoxy-6',6'-dibromo-β-D-ribo-5'-hexenofuranosyl)uracil
  参考文献：
  名称：

  Developing an efficient route to the synthesis of nucleoside 1-alkynylphosphonates

  摘要：

  A series of ribonucleoside 1-alkynylphosphonates have been synthesized using a palladium-catalyzed phosphonylation of terminal 1,1-dibromo-1-alkene nucleosidic derivatives and high selectivity for product distribution was observed during this step. Both nucleosidic and osidic pathways were explored and the corresponding optimization study is reported herein. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.064

文献信息

• 5′,6′-Nucleoside Phosphonate Analogues Architecture: Synthesis and Comparative Evaluation towards Metabolic Enzymes
  作者：Franck Gallier、Julie A. C. Alexandre、Chahrazade El Amri、Dominique Deville-Bonne、Suzanne Peyrottes、Christian Périgaud

  DOI：10.1002/cmdc.201100068

  日期：2011.6.6

  Herein, we report the synthesis of a series of ribonucleoside phosphonate derivatives isosteric to 5′‐mononucleotides, with different degrees of flexibility within the 5′,6′‐CC bond, as well as different polarities, through the introduction of hydroxy groups. The influence of these modifications on the capacity of the compounds to act as substrates for appropriate human NMP kinases, involved in nucleic

  核苷膦酸酯已被设计为稳定的5'-单核苷酸模拟物，如今被认为是一类有效的抗病毒剂。在细胞内，它们必须代谢为相应的二磷酸酯才能发挥其生物学活性。在该过程中，已经提出了由核苷单磷酸激酶（NMP激酶）催化的第一步磷酸化步骤是一个瓶颈。在这里，我们报道了一系列与5'-单核苷酸等排的核糖核苷膦酸酯衍生物的合成，在5'，6'- C内具有不同程度的柔性通过引入羟基，C键以及不同的极性。已经研究了这些修饰对化合物充当参与核酸代谢的适当人NMP激酶的底物的能力的影响。柔韧性低，以及核糖-磷结构中不存在羟基，对于有效的磷转移至关重要。在一系列嘧啶类似物中，一种衍生物被人UMP-CMP激酶磷酸化，其速率与dUMP相似，甚至优于dCMP。
• Synthesis of 3′-azido-4′-ethynyl-3′,5′-dideoxy-5′-norarabinouridine: a new anti-HIV nucleoside analogue
  作者：Mahmoud A. Amin

  DOI：10.1016/j.tet.2010.12.054

  日期：2011.3

  3'-Azido-4'-ethynyl-3',5'dideoxy-5'-norarabinouridine 10 was synthesized from commercial uridine 1 in which the key step is the opening of protected 2',3'-epoxyuridine derivative 7 by sodium azide and the hydroxymethyl at 4-position of the ribose ring are replaced by ethynyl group. (C) 2010 Elsevier Ltd. All rights reserved.
• Developing an efficient route to the synthesis of nucleoside 1-alkynylphosphonates
  作者：Maïa Meurillon、Franck Gallier、Suzanne Peyrottes、Christian Périgaud

  DOI：10.1016/j.tet.2009.05.064

  日期：2009.8

  A series of ribonucleoside 1-alkynylphosphonates have been synthesized using a palladium-catalyzed phosphonylation of terminal 1,1-dibromo-1-alkene nucleosidic derivatives and high selectivity for product distribution was observed during this step. Both nucleosidic and osidic pathways were explored and the corresponding optimization study is reported herein. (C) 2009 Elsevier Ltd. All rights reserved.