4-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-phenyl-1,2,3-triazole | 79726-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-phenyl-1,2,3-triazole
• 英文别名: 4-((3aS)-2,2-dimethyl-(3ar,6ac)-tetrahydro-furo[3,4-d][1,3]dioxol-4c-yl)-2-phenyl-2H-[1,2,3]triazole；4-((3aS)-2,2-Dimethyl-(3ar,6ac)-tetrahydro-furo[3,4-d][1,3]dioxol-4c-yl)-2-phenyl-2H-[1,2,3]triazol；4-[(3aS,4S,6aR)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-phenyltriazole
• CAS: 79726-78-6
• 化学式: C₁₅H₁₇N₃O₃
• 分子量: 287.318
• InChiKey: PEOFSLRGSFUMJA-HZSPNIEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.4
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-phenyl-4-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-2H-1,2,3-triazole 在 硫酸 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 4-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-phenyl-1,2,3-triazole
  参考文献：
  名称：

  Studies on 3-epimeric 2-hexulose phenylosazones. structure and anomeric configuration of the 3,6-anhydro-osazone derivatives obtained from d-arabino- and d-ribo-2-hexulose phenylosazone

  摘要：

  DOI：

  10.1016/s0008-6215(00)85574-3

文献信息

• Zur Kenntnis der Zucker-osazone. Die Konstitution desDiels'schen ?Anhydro-glucose-phenylosazons?
  作者：E. Hardegger、E. Schreier

  DOI：10.1002/hlca.19520350131

  日期：1952.2.1

  von Percival aufgestellten Konstitutionsformeln für das Diels'sche Anhydro-glucose-phenylosazon wurden widerlegt; diese Verbindung wurde als 3, 6-Anhydro-D-psicose-phenyl-osazon erkannt und deren Konstitution bewiesen.

  狄尔斯（Diels）和珀西瓦尔（Percival）为狄尔斯（Diels）的脱水葡萄糖-苯基osa酮建立的两个结构式已被驳斥；该化合物被认为是3,6-脱水-D-壬基-苯基-osa酮，其结构已得到证明。
• NOVEL REVERSION REACTION OF <scp>D</scp>-<i>ARABINO</i>-HEXOSE PHENYLOSOTRIAZOLE. A USEFUL MODEL IN NATURAL GLYCOSIDE AND POLYSACCHARIDE ANALYSIS
  作者：Hammed H. A. M. Hassan、Amel H. F. El-Husseiny

  DOI：10.1081/ncn-100105904

  日期：2001.9.30

  Treatment of D-arabino-hexose phenylosotriazole with conc. hydrochloric acid afforded a new type of alpha- and beta -glycosides of D-erythrose formed by reaction of the 3.6-anhydro derivative with the insitu formed 2-phenyl-4-(formylmethyl)-1,2,3-triazole.
• Studies ON Epimeric-D-<i>asabino</i>-and-D-<i>ribo</i>-tetritol-1-yl-2-phenyl-2 <i>H</i>-1,2,3-triazoles. Synthesis and Anomeric Configuration of 4-(α-and β-D-Erythrofuranosyl)-2-phenyl-2 <i>H</i>-1,2,3-Triazole <i>C</i>-Nucleoside Analogs
  作者：Mohammed A.E. Sallam、Farida F. Louis、John M. Cassady

  DOI：10.1080/07328319808004674

  日期：1998.4

  Treatment of 4-(D-arabino-tetritol-1-yl)-2-phenyl-2 H-1,2,3-triazole (1) with one mole equivalent of tosyl chloride in pyridine solution, afforded the C-nucleoside analogs, 4-(alpha-D-erythrofuranosyl)-2-phenyl-2 H-1,2,3-triazole (2) in 25% yield, as well as the byproduct 4-(4-chloro-4-deoxy-D-arabino-tetritol-1-yl)-2-phenyl-2 H-1,2,3-triazole(3). Treatment of the epimeric 4-(D-ribo-tetritol-1-yl)-2-phenyl-2 H-1,2,3-triazole(8) with tosyl chloride in pyridine solution afforded the anomeric C-nucleoside analogs, 4-(beta-D-erythrofuranosyl)-2-phenyl-2 H-1,2,3-triazole (9) in 23% yield. Similar treatment of 8 with trifluoromethanesulfonyl chloride in pyridine solution afforded 9. The structure and anomeric configuration of these compounds were determined by acylation, NMR, NOE, circular dichroism spectroscopy and mass spectrometry.