5'-O-benzoyl-2'-deoxy-5-iodouridine | 84043-31-2

• 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'-O-benzoyl-2'-deoxy-5-iodouridine
• 英文别名: [(2R,3S,5R)-3-hydroxy-5-(5-iodo-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 84043-31-2
• 化学式: C₁₆H₁₅IN₂O₆
• 分子量: 458.209
• InChiKey: WRNHWZMNGHEQNG-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-O-benzoyl-2'-deoxy-5-iodouridine 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 氯仿 为溶剂， 反应 3.0h， 生成 N3-benzoyl-5-iodo-5'-O-benzoyl-2'-deoxyuridine
  参考文献：
  名称：

  Fluorescent Labeling of (Oligo)Nucleotides by a New Fluoride Cleavable Linker Capable of Versatile Attachment Modes

  摘要：

  The development of a fluoride cleavable linker 1 for reversibly labeling (oligo)nucleotides is described here. The linker allows different ways of chemical attachment of a reporter molecule, for example, click chemistry or amide formation. The versatile attachment modes of labels are demonstrated by derivatizations with pyrene and fluorescein. Besides the synthesis of the new linker, we also show the derivatization of iodobenzene as a model compound and a nucleoside to demonstrate the applicability. Further, cleavability studies in solution and on a solid-supported oligonucleotide are shown. The linker can be applied in the synthesis of reversible terminators, useful for new DNA sequencing technologies like cyclic reversibly terminating (CRT) sequencing.

  DOI：

  10.1021/bc900542f
• 作为产物：
  描述：

  碘苷 、 苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以70%的产率得到5'-O-benzoyl-2'-deoxy-5-iodouridine
  参考文献：
  名称：

  Studies on antitumor agents. IX. Synthesis of 3'-O-benzyl-2'-deoxy-5-trifluoromethyluridine.

  摘要：

  以 2'-deoxy-5-iodouridine (3) 为原料，开发出了一种实用的 3'-O-benzyl-2'-deoxy-5-trifluoromethyluridine (1) 合成方法，这是一种用于临床测试的候选抗肿瘤药物。在四氢呋喃中用溴化苄基和氢化钠对 2'-deoxy-5-iodo-5'-O-trityluridine (14) 进行苄基化，得到 3'-O 衍生物 (16)。16 的苯甲酰化反应得到 N3-苯甲酰基衍生物 (17)。在 4-二甲氨基吡啶存在下，用溴三氟甲烷和铜粉制备三氟甲基铜，将 17 与三氟甲基铜偶联，得到 5-三氟甲基衍生物（19），该衍生物受 5-五氟乙基化合物的污染极小。对 19 进行脱保护处理后得到 1。

  DOI：

  10.1248/cpb.37.2287

文献信息

• Independent Generation and Reactivity of Thymidine Radical Cations
  作者：Huabing Sun、Marisa L. Taverna Porro、Marc M. Greenberg

  DOI：10.1021/acs.joc.7b02017

  日期：2017.10.20

  Thymidine radical cation (1) is produced by ionizing radiation and has been invoked as an intermediate in electron transfer in DNA. Previous studies on its structure and reactivity have utilized thymidine as a precursor, which limits quantitative product analysis because thymidine is readily reformed from 1. In this investigation, radical cation 1 is independently generated via β-heterolysis of a pyrimidine

  胸苷自由基阳离子（1）是通过电离辐射产生的，已被称为DNA中电子转移的中间体。以前对其结构和反应性的研究已使用胸苷作为前体，因为胸腺嘧啶很容易从1进行重整，因此它限制了定量产物的分析。在该研究中，自由基阳离子1是通过对由芳基硫醚光化学生成的嘧啶自由基进行β杂解而独立生成的。胸苷是pH 7.2时从1的主要产物（33％）。胸苷二醇和相应的5-羟基过氧化物的非对映异构体混合物，其捕集量为1形成。观察到归因于C 1-甲基1的去质子化的产物例如5-甲酰基-2'-脱氧尿苷的产率显着降低。独立生成的N3甲基类似物1（NMe- 1）产生的从水捕集衍生的产物明显更高的产率，和在比这些可归因于NMe-的C5-甲基脱质子高得多的产率形成这些产品1。但是，N3-甲基胸苷是主要产物，当在过量硫醇的存在下生成自由基阳离子时，N3-甲基胸苷的产率高达70％。外源试剂对产物分布的影响与扩散性自由基阳离子的形成是一致的（1，NMe-
• Chem. Pharm. Bull. 1989, 37, 2287-2292
  作者：

  DOI：——

  日期：——
• YAMASHITA, JUN-ICHI;MATSUMOTO, HIROSHI;KOBAYASHI, KAZUHIRO;NOGUCHI, KAZUH+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 2287-2292
  作者：YAMASHITA, JUN-ICHI、MATSUMOTO, HIROSHI、KOBAYASHI, KAZUHIRO、NOGUCHI, KAZUH+

  DOI：——

  日期：——
• Fluorescent Labeling of (Oligo)Nucleotides by a New Fluoride Cleavable Linker Capable of Versatile Attachment Modes
  作者：Diana C. Knapp、Jennifer D’Onofrio、Joachim W. Engels

  DOI：10.1021/bc900542f

  日期：2010.6.16

  The development of a fluoride cleavable linker 1 for reversibly labeling (oligo)nucleotides is described here. The linker allows different ways of chemical attachment of a reporter molecule, for example, click chemistry or amide formation. The versatile attachment modes of labels are demonstrated by derivatizations with pyrene and fluorescein. Besides the synthesis of the new linker, we also show the derivatization of iodobenzene as a model compound and a nucleoside to demonstrate the applicability. Further, cleavability studies in solution and on a solid-supported oligonucleotide are shown. The linker can be applied in the synthesis of reversible terminators, useful for new DNA sequencing technologies like cyclic reversibly terminating (CRT) sequencing.
• Studies on antitumor agents. IX. Synthesis of 3'-O-benzyl-2'-deoxy-5-trifluoromethyluridine.
  作者：Jun-ichi YAMASHITA、Hiroshi MATSUMOTO、Kazuhiro KOBAYASHI、Kazuharu NOGUCHI、Mitsugi YASUMOTO、Tohru UEDA

  DOI：10.1248/cpb.37.2287

  日期：——

  A practical synthesis of 3'-O-benzyl-2'-deoxy-5-trifluoromethyluridine (1), a candidate antitumor agent for clinical testing, was developed from 2'-deoxy-5-iodouridine (3). Benzylation of 2'-deoxy-5-iodo-5'-O-trityluridine (14) with benzyl bromide and sodium hydride in tetrahydrofuran gave the 3'-O-derivative (16). Benzoylation of 16 afforded the N3-benzoyl derivative (17). Coupling of 17 with trifluoromethylcopper, prepared from bromotrifluoromethane and copper powder in the presence of 4-dimethylaminopyridine, gave the 5-trifluoromethyl derivative (19) minimally contaminated with the 5-pentafluoroethyl compound. Deprotection of 19 furnished 1.

  以 2'-deoxy-5-iodouridine (3) 为原料，开发出了一种实用的 3'-O-benzyl-2'-deoxy-5-trifluoromethyluridine (1) 合成方法，这是一种用于临床测试的候选抗肿瘤药物。在四氢呋喃中用溴化苄基和氢化钠对 2'-deoxy-5-iodo-5'-O-trityluridine (14) 进行苄基化，得到 3'-O 衍生物 (16)。16 的苯甲酰化反应得到 N3-苯甲酰基衍生物 (17)。在 4-二甲氨基吡啶存在下，用溴三氟甲烷和铜粉制备三氟甲基铜，将 17 与三氟甲基铜偶联，得到 5-三氟甲基衍生物（19），该衍生物受 5-五氟乙基化合物的污染极小。对 19 进行脱保护处理后得到 1。