5-amino-4-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuanosyl)-v-triazole | 99249-20-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: 5-amino-4-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuanosyl)-v-triazole
• 英文别名: 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carbonitrile；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-amino-4-cyanotriazol-1-yl)oxolan-2-yl]methyl acetate
• CAS: 99249-20-4
• 化学式: C₁₄H₁₇N₅O₇
• 分子量: 367.318
• InChiKey: DLPKCEMGRBKGKI-HKUMRIAESA-N

物化性质

• 沸点：
  577.2±60.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  169
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-amino-4-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuanosyl)-v-triazole 在 吡啶 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 15.0h， 生成 7-[(furan-2-yl)methylamino]-3-β-D-ribofuranosyl-3H-[1,2,3]triazole[4,5-d]-pyrimidine
  参考文献：
  名称：

  激动素核苷及其类似物的变温核磁共振结构研究

  摘要：

  摘要 合成了激动素核苷及其四种碱基修饰的类似物，并采用多核一维和二维变温核磁共振技术研究了它们在溶液中的结构。在较低的温度下，发现激动素核苷作为两种不同构象异构体的混合物存在，这是由于围绕 C6-N6 键的旋转受限。对于 8-氮激动素核苷和 2-氟激动素核苷，在室温下观察到两个旋转异构体的存在。

  DOI：

  10.1016/j.molstruc.2019.05.112
• 作为产物：
  描述：

  5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-v-triazole-4-carboxamide 在 吡啶 、 对甲苯磺酰氯 作用下， 反应 24.0h， 以59%的产率得到5-amino-4-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuanosyl)-v-triazole
  参考文献：
  名称：

  5-Ethynyl-1-β-d-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (ETCAR) and its analogues: Synthesis and cytotoxic properties

  摘要：

  Efficient Pd(0)-catalysed synthesis of 5-alkynyl-1-beta-D-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide depends on the presence of different protecting groups of the ribose moiety. Peracetylated 5-iodo substrate (15) couples with terminal alkynes or trimethyl-[(tributylstannyl)ethynyl] silane in 50-71% and 72% yield (ETCAR), respectively, although its hydrodehalogenation to 19 is noticeable. On the other hand, hydrodehalogenation of acetonide (16) predominates over coupling with terminal alkyne and slightly decreases a yield of cross-coupling reaction with trimethyl[(tributylstannyl)ethynyl] silane. Alternative conditions of reaction with terminal alkynes, to exclude so far identified hydride sources to produce hydridopalladium species, have been established for acetonide 16 and allowed to achieve 72% of coupling. Fluoromethyl derivative (42) was prepared from its 5-hydroxymethyl precursor by fluorination with DAST. Additionally, X-ray structural analysis of 42 was performed. All 1,2,3-triazolonucleosides and two synthesized cycloSal-pronucleotides were evaluated for cytotoxic activity against K562, HeLa and HUVEC cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.050

文献信息

• Total synthesis of (4R)- and (4S)-5,6-dihydro-1-.beta.-D-ribofuranosyl-4H-pyrazolo[3,4-d][1,3]diazepin-4-ol and (8R)- and (8S)-7,8-dihydro-3-.beta.-D-ribofuranosyl-6H-v-triazolo[4,5-d][1,3]diazepin-8-ol: two heterocyclic analogs of the nucleoside antibiotic coformycin
  作者：Oscar L. Acevedo、Steven H. Krawczyk、Leroy B. Townsend

  DOI：10.1021/jo00357a020

  日期：1986.4