3',5'-Di-O-benzoyl-2'-bromo-2'deoxyuridine | 62232-29-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3',5'-Di-O-benzoyl-2'-bromo-2'deoxyuridine
• 英文别名: [(2R,3R,4R,5R)-3-benzoyloxy-4-bromo-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 62232-29-5
• 化学式: C₂₃H₁₉BrN₂O₇
• 分子量: 515.317
• InChiKey: CRTYIZYLWDBYLH-VBSBHUPXSA-N

物化性质

• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3',5'-Di-O-benzoyl-2'-bromo-2'deoxyuridine 在 偶氮二异丁腈 、 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 5.0h， 生成 2'-α-C-allenyl-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of 2′-α-C-allenyl-2′-deoxyuridine: An analogue of 2′-azido-2′-deoxyuridine, known inhibitor of ribonucleotide diphosphate reductase (RDPR)

  摘要：

  The 1,2-propadienyl (allenyl) group was introduced by means of a radical reaction at the 2'-alpha-C position of uridine to prepare the title compound as a novel analogue of 2'-azido-2'-deoxyuridine, a known inhibitor of RDPR. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00917-x
• 作为产物：
  描述：

  2,2'-脱水尿苷 在 三乙胺 、 三氟乙酸 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 3',5'-Di-O-benzoyl-2'-bromo-2'deoxyuridine
  参考文献：
  名称：

  Synthesis of 2′-α-C-allenyl-2′-deoxyuridine: An analogue of 2′-azido-2′-deoxyuridine, known inhibitor of ribonucleotide diphosphate reductase (RDPR)

  摘要：

  The 1,2-propadienyl (allenyl) group was introduced by means of a radical reaction at the 2'-alpha-C position of uridine to prepare the title compound as a novel analogue of 2'-azido-2'-deoxyuridine, a known inhibitor of RDPR. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00917-x

文献信息

• Sonochemical and triethylborane-induced tin deuteride reduction for the highly stereoselective synthesis of (2′R)-[2′-2H]-2′-deoxyribonucleosides from 2′-functionalized ribonucleosides
  作者：Etsuko Kawashima、Yukio Aoyama、Takeshi Sekine、Eiichi Nakamura、Masatsune Kainosho、Yoshimasa Kyogoku、Yoshiharu Ishido

  DOI：10.1016/s0040-4039(00)91784-2

  日期：1993.2

  (Bu3SnH)-H-2-reduction of a 2'-bromo-2'-deoxyuridine benzoate under high-intensity ultrasound irradiation at -71-degrees-C resulted in highly efficient deuterium incorporation to afford a 96:4 mixture of (2'R)- and (2'S)-[2,-H-2]-2'-deoxyuridine. The use of both Et3B, as an alternative radical generator, and 2'-bromo-2'-deoxy-3',5'-O-TPDS-ribonucleosides made it feasible to perform the reaction in a preparative scale in addition to an excellent stereoselectivity (>99:1).

  在-71摄氏度下，通过高强度超声波辐照，(Bu3SnH)对2'-溴-2'-脱氧尿苷苯甲酸酯进行H-2还原，成功实现了高效氘掺入，生成了(2'R)-和(2'S)-[2,-H-2]-2'-脱氧尿苷的96:4混合物。同时，使用乙基三甲基锡（Et3B）作为替代的自由基生成剂，以及2'-溴-2'-脱氧-3',5'-O-TPDS-核糖核苷作为反应物，使得该反应不仅能在制备规模上进行，而且还具有极高的立体选择性（>99:1）。
• 5-(E)-bromovinyl uracil analogues and related pyrimidine nucleosides as anti-viral agents and methods of use
  申请人：——

  公开号：US20040053891A1

  公开（公告）日：2004-03-18

  The present invention relates to pyrimidine nucleoside compounds and their use to treat viral infections of Varicella Zoster Virus, Epstein Barr Virus and Kaposi's Sarcoma virus, also known as HV-8 and related complications of these viral infections. In another aspect of the present invention, the use of one or more nucleoside compound to increase the retention or half-life of 5-fluorouracil (FU) in patients is also described.

  本发明涉及嘧啶核苷化合物及其用于治疗水痘-带状疱疹病毒、艾普斯坦-巴尔病毒和卡波西肉瘤病毒等病毒感染及其相关并发症的应用。在本发明的另一方面，还描述了使用一种或多种核苷化合物以增加5-氟尿嘧啶（FU）在患者体内的保留时间或半衰期。
• Sonochemical and Triethylborane-Induced Tin Deuteride Reduction for the Highly Diastereoselective Synthesis of (2'R)-2'-Deoxy[2'-2H]ribonucleoside Derivatives
  作者：Etsuko Kawashima、Yukio Aoyama、Takeshi Sekine、Masayoshi Miyahara、Mohamed F. Radwan、Eiichi Nakamura、Masatsune Kainosho、Yoshimasa Kyogoku、Yoshiharu Ishido

  DOI：10.1021/jo00126a058

  日期：1995.10

  For the NMR spectroscopic conformational analysis of a sugar moiety in a DNA complex with a protein or a drug, (2'R)- and/or (2'S)-2'-deoxy[2'-H-2]ribonucleoside derivatives with high purity are useful. To develop a highly diastereoselective and efficient method for the synthesis of(2'R)-2'-deoxy[2'-H-2]ribonucleoside derivatives, studies of leaving groups (OPTC, Br) at the 2' position of nucleosides, of the effects of reaction temperature on diastereoselectivity, of radical generation (ultrasound irradiation, Et(3)B) at temperatures as low as -70 degrees C, and of protecting groups for the 3' and 5' hydroxyl groups (benzoate, TPDS) of nucleosides were carried out. Bu(3)Sn(2)H-reductive deuteration of 3',5'-di-0-benzoyl-2'-bromo-2'-deoxyuridine under high-intensity ultrasound irradiation at -71 degrees C induced notably efficient deuterium incorporation to afford a highly diastereoselective 3',5'-di-0-benzoyl-2'-deoxy[2'-H-2]uridin [(2'R):(2'S) = 96:4]. The use of Et(3)B, as an alternative radical generator, toward 2'-bromo-2'-deoxy-3',5'-0-TPDS-ribonucleosides at <--70 degrees C made it feasible to perform the reaction on a preparative scale, and provided excellent diastereoselectivity (2'-deoxyadenosine, thymidine, and 2'-deoxyuridine derivatives >99:1 which were converted to (2'R)-2'-deoxy[2'-H-2]cytidine derivatives, guanosine derivative = 91:9).
• 5-(E)-BROMOVINYL URACIL ANALOGUES AND RELATED PYRIMIDINE NUCLEOSIDES AS ANTI-VIRAL AGENTS AND METHODS OF USE
  申请人：Yale University

  公开号：EP1204415B1

  公开（公告）日：2010-09-08
• Synthesis of 2′-α-C-allenyl-2′-deoxyuridine: An analogue of 2′-azido-2′-deoxyuridine, known inhibitor of ribonucleotide diphosphate reductase (RDPR)
  作者：Mélanie Ethève - Quelquejeu、Jean-Marc Valéry

  DOI：10.1016/s0040-4039(99)00917-x

  日期：1999.6

  The 1,2-propadienyl (allenyl) group was introduced by means of a radical reaction at the 2'-alpha-C position of uridine to prepare the title compound as a novel analogue of 2'-azido-2'-deoxyuridine, a known inhibitor of RDPR. (C) 1999 Elsevier Science Ltd. All rights reserved.