N³-benzoyluridine | 86988-30-9

• 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: N³-benzoyluridine
• 英文别名: 3-benzoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 86988-30-9
• 化学式: C₁₆H₁₆N₂O₇
• 分子量: 348.312
• InChiKey: OBAWYLHRLPHDSX-BPGGGUHBSA-N

物化性质

• 沸点：
  603.7±65.0 °C(Predicted)
• 密度：
  1.598±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N³-benzoyluridine 在 ammonium hydroxide 作用下， 反应 0.42h， 生成 尿嘧啶核苷
  参考文献：
  名称：

  Welch, Christopher J.; Chattopadhyaya, Jyoti, Heterocycles, 1984, vol. 21, # 2, p. 541

  摘要：

  DOI：
• 作为产物：
  描述：

  2',3',5'-tris-O-(trimethylsilyl)uridine 在 吡啶 、 水 作用下， 反应 48.08h， 生成 N³-benzoyluridine
  参考文献：
  名称：

  An Improved Transient Method for the Synthesis ofN-Benzoylated Nucleosides

  摘要：

  The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.

  DOI：

  10.1081/scc-120017200

文献信息

• Mechanism of Charge Transport in DNA:  Internally-Linked Anthraquinone Conjugates Support Phonon-Assisted Polaron Hopping
  作者：Danith Ly、Laurie Sanii、Gary B. Schuster

  DOI：10.1021/ja991753s

  日期：1999.10.1

  complement. The AQ-conjugates were designed to have GG steps disposed symmetrically about the AQ intercalation site. The distance dependence of reaction efficiency at GG steps following AQ irradiation was measured by means of an AQ-containing 71 mer having 7 GG steps. The efficiency of reaction in this sequence falls off exponentially with a distance dependence of 0.071 A-1. AQ-containing conjugates

  制备了一系列含蒽醌 (AQ) 的 DNA 偶联物。在每种情况下，AQ 都与尿苷的 2'-氧相连。物理和光谱数据表明 AQ 嵌入在尿嘧啶 3' 侧的双链 DNA 中。用紫外线照射 AQ-DNA 偶联物会导致含 AQ 链及其互补链在 GG 步骤处需要哌啶的链断裂。AQ 偶联物被设计为具有围绕 AQ 嵌入位点对称布置的 GG 台阶。AQ 辐照后 GG 步骤的反应效率的距离依赖性是通过具有 7 个 GG 步骤的含 AQ 71 聚体来测量的。该序列中的反应效率呈指数下降，距离相关性为 0.071 A-1。制备含有 AQ 的偶联物，其中包含 7、不同位置的 8-dihydro-8-oxoguanines (8-OxoG)。8-OxoG 的氧化电位低于任何正常 DNA 碱基，可作为迁移自由基阳离子的陷阱。天...
• Studies on Steric and Electronic Control of 2‘−3‘ Phosphoryl Migration in 2‘-Phosphorylated Uridine Derivatives and Its Application to the Synthesis of 2‘-Phosphorylated Oligouridylates
  作者：Mitsuo Sekine、Hiroyuki Tsuruoka、Shin Iimura、Hiroshi Kusuoku、Takeshi Wada、Kiyotaka Furusawa

  DOI：10.1021/jo952073k

  日期：1996.1.1

  phosphitylation with bis(2-cyano-1,1-dimethylethoxy)(diethylamino)phosphine followed by sulfurization. Treatment of the 2'-thiophosphorylated product 15 with (HF)(x)().Py in THF gave exclusively the 3',5'-unprotected uridine derivative 16a. Compound 16a was converted to the phosphoramidite unit 22 via a two-step reaction. This building block was used for the solution phase synthesis of U(2'-p)pU (29)

  对于通过使用新的亚磷酰胺结构单元合成2'-磷酸化的低聚吡啶二酸酯，已经研究了几种掩蔽的磷酰基作为2'-磷酸酯前体，当3'羟基保护基必须是3'羟基时，不应将其迁移到3'位置。去除亚磷酰胺残基，将其引入3'-位。结果，发现双（2-氰基-1,1-二甲基乙氧基）硫代磷酰基（BCMETP）是最合适的2'-磷酸盐前体。该硫代磷酰基可通过与双（2-氰基-1，1-二甲基乙氧基）（二乙氨基）膦进行磷酸化，然后硫化而引入3'，5'-甲硅烷基化尿苷衍生物7的2'-羟基。用（HF）（x）（）。Py在THF中处理2'-硫代磷酸化产物15，仅得到3'，5' -未保护的尿苷衍生物16a。化合物16a通过两步反应被转化为亚磷酰胺单元22。该构件用于U（2'-p）pU（29）和U（2'-ps）pU（30）的溶液相合成。通过在N，O-双（三甲基甲硅烷基）乙酰胺（BSA）存在下用DBU处理，从完全保护的衍生物25中有效除去2-
• Regioselective protection of the 2′-hydroxyl group of N-acyl-3′,5′-O-di(t-butyl)silanediylnucleoside derivatives by use of t-BuMgCl and 2-(trimethylsilyl)ethoxymethyl chloride
  作者：Takeshi Wada、Masanori Tobe、Takashi Nagayama、Kiyotaka Furusawa、Mitsuo Sekine

  DOI：10.1016/0040-4039(95)00130-5

  日期：1995.3

  Regioselective 2′-O-protection of N-protected 3′,5′-O-di(t-butyl)silanediylribonucleoside derivatives with the 2-(trimethylsilyl)ethoxymethyl (SEM) group has been achieved by use of t-BuMgCl and 2-(trimethylsilyl)ethoxymethyl chloride. The former was used as a base. The 2′-O-SEM protected ribonucleoside derivatives were converted via a three-step reaction into the corresponding phosphoramidite building

  通过使用t -BuMgCl和2实现了N保护的3'，5'- O-二（叔丁基）硅烷二基核糖核苷衍生物具有2-（三甲基甲硅烷基）乙氧基甲基（SEM）基团的区域选择性2'- O-保护。-（三甲基甲硅烷基）乙氧基甲基氯。前者被用作基础。通过三步反应将2'- O- SEM保护的核糖核苷衍生物以良好的总收率转化为相应的亚磷酰胺结构单元。
• An Improved Transient Method for the Synthesis of<i>N</i>-Benzoylated Nucleosides
  作者：Xue-Feng Zhu、Howard J. Williams、A. Ian Scott

  DOI：10.1081/scc-120017200

  日期：2003.1.5

  The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.
• Welch, Christopher J.; Chattopadhyaya, Jyoti, Heterocycles, 1984, vol. 21, # 2, p. 541
  作者：Welch, Christopher J.、Chattopadhyaya, Jyoti

  DOI：——

  日期：——