2',3',5'-tri-O-acetyl-4-(1,2,4-triazol-1-yl)uridine | 82913-19-7

• 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: 2',3',5'-tri-O-acetyl-4-(1,2,4-triazol-1-yl)uridine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 82913-19-7
• 化学式: C₁₇H₁₉N₅O₈
• 分子量: 421.367
• InChiKey: WLVWKXFSZYCKGR-DTZQCDIJSA-N

物化性质

• 熔点：
  184-187 °C
• 沸点：
  605.5±65.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-acetyl-4-(1,2,4-triazol-1-yl)uridine 在 氨 作用下， 以 ammonium hydroxide 、 乙醇 为溶剂， 生成 胞苷
  参考文献：
  名称：

  4-Substituted Uridine 5′-Triphosphates as Agonists of the P_2Y2Purinergic Receptor

  摘要：

  Uridine 5'-O-triphosphate (UTP) is a potent agonist of the purinergic receptor designated P-2Y2. UTP is rapidly metabolized in human tissue. To find a compound with similar activity that may be more slowly metabolized, a series of 4-substituted uridine 5'-triphosphates were prepared and evaluated in a P-2Y2 receptor second messenger assay.

  DOI：

  10.1080/07328319708006141
• 作为产物：
  描述：

  尿嘧啶核苷 在 4-氯苯基二氯磷酸酯 作用下， 以 吡啶 为溶剂， 反应 21.0h， 生成 2',3',5'-tri-O-acetyl-4-(1,2,4-triazol-1-yl)uridine
  参考文献：
  名称：

  4-Substituted Uridine 5′-Triphosphates as Agonists of the P_2Y2Purinergic Receptor

  摘要：

  Uridine 5'-O-triphosphate (UTP) is a potent agonist of the purinergic receptor designated P-2Y2. UTP is rapidly metabolized in human tissue. To find a compound with similar activity that may be more slowly metabolized, a series of 4-substituted uridine 5'-triphosphates were prepared and evaluated in a P-2Y2 receptor second messenger assay.

  DOI：

  10.1080/07328319708006141

文献信息

• Nucleosides. Part LIX. The 2-(4-nitrophenyl)ethylsulfonyl (Npes) Group: A New Type of Protection in Nucleoside Chemistry
  作者：Magdalena Pfister、Helga Schirmeister、Marion Mohr、Silke Farkas、Klaus-Peter Stengele、Tilman Reiner、Martin Dunkel、Surendra Gokhale、Ramamurthy Charubala、Wolfgang Pfleiderer

  DOI：10.1002/hlca.19950780706

  日期：1995.11.1

  The 2-(4-nitrophenyl)ethylsulfonyl (npes) group is developed as a new sugar OH-blocking group in the ribonucleoside series. Its cleavage can be performed in a β-eliminating process under aprotic conditions using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the most effective base. Since sulfonates do not show acyl migration, partial protection of 1,2-cis-diol moieties is possible leading to new types

  2-（4-硝基苯基）乙基磺酰基（npes）基团被开发为核糖核苷系列中新的糖OH封闭基团。可以在非质子条件下以β-消除过程进行裂解，使用1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）作为最有效的碱基。由于磺酸盐不显示酰基迁移，因此可能会部分保护1,2-顺式-二醇部分，从而导致新型的寡核苷酸构建基团。一系列由Markiewicz保护的核糖核苷1-10转化为它们的2'- O- [2-（4-硝基苯基）乙基磺酰基]衍生物29-38，其中5'-OSi键可通过酸水解裂解形成39- 45。随后的单甲氧基三苯甲基化导致46-50，和脱甲硅基，得到5'- ø - （单甲氧）-2'- ö - [2-（4-硝基苯基）乙基磺酰基]核糖核苷51-55。酸处理去除三苯甲基也不会伤害npes组（56-58）。完全封闭的2'- O- [2-（4-硝基苯基）乙基磺酰基]核糖核苷96-102的明确合成是通过相应的3'-
• Synthesis of Uridine Derivatives Containing Amino Acid Residues
  作者：Yu Gao、Peng Zhang、Ling Wu、Teruo Matsuura、Jiben Meng

  DOI：10.1081/scc-120021984

  日期：2003.1.8

  Abstract Convenient synthesis of uridine derivatives containing amino acid residues were carried out successfully by reacting triazolated uridine with the hydrochloride salts of some amino acid esters, which provides a general method for the direct introduction of amino acid group onto nucleoside residue.

  摘要 通过三唑化尿苷与某些氨基酸酯的盐酸盐反应，成功合成了含氨基酸残基的尿苷衍生物，为将氨基酸基团直接引入核苷残基提供了通用方法。
• Synthesis of Oligoribonucleotides Containing 4‐Thiouridine Using the Convertible Nucleoside Approach and the 1‐(2‐Fluorophenyl)‐4‐Methoxypiperidin‐4‐yl Group
  作者：Anna Aviñó、Ramon Güimil García、Ramon Eritja

  DOI：10.1081/ncn-200034044

  日期：2004.1.1

  Oligoribonucleotides containing 4‐thiouridine were prepared using the Fpmp group for protection of the 2′‐OH. Two uridine derivatives with the 1,2,4‐triazolyl and the 2‐nitrophenyl groups at position 4 were used to obtain 4‐thiouridine by postsynthetic substitution with sodium hydrogen sulfide. Both uridine derivatives allow the preparation of the desired oligonucleotides in good yields.

  使用 Fpmp 基团制备含有 4-硫尿苷的寡核糖核苷酸以保护 2'-OH。使用在 4 位具有 1,2,4-三唑基和 2-硝基苯基的两种尿苷衍生物，通过硫化氢钠的合成后取代获得 4-硫尿苷。两种尿苷衍生物都能以良好的产率制备所需的寡核苷酸。
• Chemical conversion of uridine into 4-thiouridine via the 4-(1,2,4-triazol-1-yl)pyrimidin-2(1H)-one intermediate
  作者：Wing L. Sung

  DOI：10.1039/c39820000522

  日期：——

  In an aqueous solution of sodium hydrosulphide at room temperature, 4-(1,2,4-triazol-1-yl)-1-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)pyrimidin-2(1H)-one, prepared from uridine, is converted into the 4-thiopyrimidin-2(1H)-one derivative which can be deacetylated to yield 4-thiouridine.

  在室温下的硫化氢钠水溶液中，4-（1,2,4-三唑-1-基）-1-（2'，3'，5'-三-O-乙酰基-β - D-呋喃呋喃糖基由尿苷制备的）嘧啶-2（1 H）-一被转化为4-硫嘧啶-2（1 H）-一衍生物，该衍生物可被脱乙酰化以产生4-硫尿苷。
• Reaction between nucleoside base residues and the phosphorylating agent derived from 1-hydroxybenzotriazole and 2-chloroprenyl phosphorodichloridate
  作者：Colin B. Reese、Keith H. Richards

  DOI：10.1016/s0040-4039(00)98973-1

  日期：1985.1

  In the presence of 1-methylimidazole, 2--acyl guanine (as in ), thymine (as in ) and uracil (as in ) residues react readily with the phosphorylating agent derived from 2-chlorophenyl phosphorodichloridate () and 1-hydroxybenzotriazole.

  在1-甲基咪唑，2-酰基鸟嘌呤（如），胸腺嘧啶（如）和尿嘧啶（如）的存在下，残基容易与衍生自2-氯苯基二氯磷酸酯（）和1-羟基苯并三唑的磷酸化剂反应。