2-phenyl-4-(D-arabino-1',2',3'-trihydroxy-4'-O-p-toluenesulfonylbutyl)-2H-1,2,3-triazole | 99099-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-4-(D-arabino-1',2',3'-trihydroxy-4'-O-p-toluenesulfonylbutyl)-2H-1,2,3-triazole
• 英文别名: D-(1R)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-O⁴-(toluene-4-sulfonyl)-erythritol；D-(1R)-1-(2-Phenyl-2H-[1,2,3]triazol-4-yl)-O⁴-(toluol-4-sulfonyl)-erythrit；[(2R,3S,4R)-2,3,4-trihydroxy-4-(2-phenyltriazol-4-yl)butyl] 4-methylbenzenesulfonate
• CAS: 99099-78-2
• 化学式: C₁₉H₂₁N₃O₆S
• 分子量: 419.458
• InChiKey: WHXCEDUFWVSHQA-GUDVDZBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-(D-arabino-1',2',3'-trihydroxy-4'-O-p-toluenesulfonylbutyl)-2H-1,2,3-triazole 在 氯仿 、 sodium methylate 作用下， 生成 (1S,2R)-1-((R)-oxiranyl)-2-(2-phenyl-2H-[1,2,3]triazol-4-yl)-ethane-1,2-diol
  参考文献：
  名称：

  知道糖osazone。第二次沟通。约3,6-和5,6-脱水-D-果糖-苯基三唑

  摘要：

  从D-果糖-苯基三唑开始，制备了稳定的3，6-脱水-和反应性5，6-脱水-D-果糖-苯基三唑。可以通过明显进行转化（主要是转化为6位取代的D-果糖-苯基磺基三唑）并与其他来源的制剂和已知组成进行比较来证明这两种脱水三唑的组成。D-果糖-苯基三唑的甲苯磺酸化的三种副产物的组成尚未阐明。

  DOI：

  10.1002/hlca.19520350228
• 作为产物：
  描述：

  glucosazone 在 吡啶 、 copper(II) sulfate 作用下， 反应 7.5h， 生成 2-phenyl-4-(D-arabino-1',2',3'-trihydroxy-4'-O-p-toluenesulfonylbutyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis and antiviral activity evaluation of novel 2-phenyl-4-(d-arabino-4′-cycloaminobutyl)triazoles: acyclonucleosides containing unnatural bases

  摘要：

  Five 2-phenyl-4-(D-arabino-4'-cycloamino-3'-hydroxy-O-1',2'-isopropylidene-butyl)-2H-1,2,3-triazoles, acyclonucleosides containing unnatural bases have been synthesised by opening of the epoxide ring of 2-phenyl-4-(D-arabino-3',4'-epoxy-O-1',2'-isopropylidenebutyl)-2H-1,2,3-triazole with the corresponding cyclic amines in 70-85% yields. The starting arabino-epoxytriazole was prepared in five steps starting from D-glucose in an overall yield of 15%. All the five triazolylacyclonucleosides were unambiguously identified on the basis of their spectral data. The structure of one of the intermediates, that is 2-phenyl-4-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-2H-1,2,3-triazole was confirmed by its X-ray crystallographic studies. These acyclonucleosides were subjected to antiviral activity evaluation in CEM-SS cell-based anti HIV assay with the lymphocytropic virus strains HIV-1(IIIB) and HIV-1(RF).

  DOI：

  10.1016/s0968-0896(01)00349-2

文献信息

• Zur Kenntnis der Zucker-osazone. 2. Mitteilung. Über das 3,6- und das 5,6-Anhydro-D-fructose-phenylosotriazol
  作者：E. Hardegger、E. Schreier

  DOI：10.1002/hlca.19520350228

  日期：1952.2.1

  Ausgehend von D-Fructose-phenylosotriazol wurden das beständige 3, 6-Anhydro- und das reaktionsfähige 5, 6-Anhydro-D-fructose-phenylosotriazol hergestellt. Die Konstitution der beiden Anhydrotriazole konnte durch eindeutig verlaufende Umwandlungen — vorwiegend zu 6-substituierten D-Fructose-phenylosotriazolen — und Vergleich mit Präparaten anderer Herkunft und bekannter Konstitution bewiesen werden. Drei Nebenprodukte

  从D-果糖-苯基三唑开始，制备了稳定的3，6-脱水-和反应性5，6-脱水-D-果糖-苯基三唑。可以通过明显进行转化（主要是转化为6位取代的D-果糖-苯基磺基三唑）并与其他来源的制剂和已知组成进行比较来证明这两种脱水三唑的组成。D-果糖-苯基三唑的甲苯磺酸化的三种副产物的组成尚未阐明。
• Synthesis and antiviral activity evaluation of novel 2-phenyl-4-(d-arabino-4′-cycloaminobutyl)triazoles: acyclonucleosides containing unnatural bases
  作者：. Himanshu、Rahul Tyagi、Carl E. Olsen、William Errington、Virinder S. Parmar、Ashok K. Prasad

  DOI：10.1016/s0968-0896(01)00349-2

  日期：2002.4

  Five 2-phenyl-4-(D-arabino-4'-cycloamino-3'-hydroxy-O-1',2'-isopropylidene-butyl)-2H-1,2,3-triazoles, acyclonucleosides containing unnatural bases have been synthesised by opening of the epoxide ring of 2-phenyl-4-(D-arabino-3',4'-epoxy-O-1',2'-isopropylidenebutyl)-2H-1,2,3-triazole with the corresponding cyclic amines in 70-85% yields. The starting arabino-epoxytriazole was prepared in five steps starting from D-glucose in an overall yield of 15%. All the five triazolylacyclonucleosides were unambiguously identified on the basis of their spectral data. The structure of one of the intermediates, that is 2-phenyl-4-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-2H-1,2,3-triazole was confirmed by its X-ray crystallographic studies. These acyclonucleosides were subjected to antiviral activity evaluation in CEM-SS cell-based anti HIV assay with the lymphocytropic virus strains HIV-1(IIIB) and HIV-1(RF).