4,5-diphenyl-3-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosylthio)-4H-1,2,4-triazole | 956922-73-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-diphenyl-3-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosylthio)-4H-1,2,4-triazole
• 英文别名: 4,5-diphenyl-4H-1,2,4-triazol-3-yl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-1-thio-beta-D-glucopyranoside；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-[(4,5-diphenyl-1,2,4-triazol-3-yl)sulfanyl]oxan-2-yl]methyl acetate
• CAS: 956922-73-9
• 化学式: C₂₈H₃₀N₄O₈S
• 分子量: 582.634
• InChiKey: IXWQRHYNPGPQKG-CMSSPHMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4,5-二苯基-4H-1,2,4-噻唑-3-硫醇 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.05h， 以89%的产率得到4,5-diphenyl-3-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosylthio)-4H-1,2,4-triazole
  参考文献：
  名称：

  Synthesis of 5‐Aryl‐3‐Glycosylthio‐4‐Phenyl‐4H‐1,2,4‐Triazoles and Their Acyclic Analogs Under Conventional and Microwave Conditions

  摘要：

  Under microwave irradiation (MWI), 4-phenyl-5-substituted-4H-1,2,4-triazole-3-thiol derivatives 7 and 8 were synthesized in a good yield by intramolecular cyclization of the aroyl phenyl thiosemicarbazides 5 and 6. The respective triazolylglycosides (Str-glycosides) 12-17 were obtained by reaction of triazoles 7 and 8 with glycosyl halides 9-11 in dry acetone in the presence of potassium carbonate as base under both conventional and MWI conditions. Alkylation of 7 and 8 with haloalchols 18-20 in boiling ethanolic solution containing sodium ethoxide as a base gave the corresponding alkylated analogs 21-26. MWI conditions led to higher yield in shorter reaction time than the conventional method. Treatment of 26 with tosyl chloride gave the unexpected product 29 and not 27 or 28. Oxidation of 26 with sodium metaperiodate afforded triazole 8 and not the aldehyde 30. Attempted glycosylation and alkylation of the phenolic OH group in triazole 8 were unsuccessful; this was proved by theoretical calculations using the AM1 semi-empirical method.

  DOI：

  10.1080/07328300802030795

文献信息

• Synthesis of 5‐Aryl‐3‐Glycosylthio‐4‐Phenyl‐4H‐1,2,4‐Triazoles and Their Acyclic Analogs Under Conventional and Microwave Conditions
  作者：El Sayed H. El‐Ashry、Nagwa Rashed、Laila F. Awad、El Sayed Ramadan、Somia M. Abdel‐Maggeed、Nagat Rezki

  DOI：10.1080/07328300802030795

  日期：2008.5

  Under microwave irradiation (MWI), 4-phenyl-5-substituted-4H-1,2,4-triazole-3-thiol derivatives 7 and 8 were synthesized in a good yield by intramolecular cyclization of the aroyl phenyl thiosemicarbazides 5 and 6. The respective triazolylglycosides (Str-glycosides) 12-17 were obtained by reaction of triazoles 7 and 8 with glycosyl halides 9-11 in dry acetone in the presence of potassium carbonate as base under both conventional and MWI conditions. Alkylation of 7 and 8 with haloalchols 18-20 in boiling ethanolic solution containing sodium ethoxide as a base gave the corresponding alkylated analogs 21-26. MWI conditions led to higher yield in shorter reaction time than the conventional method. Treatment of 26 with tosyl chloride gave the unexpected product 29 and not 27 or 28. Oxidation of 26 with sodium metaperiodate afforded triazole 8 and not the aldehyde 30. Attempted glycosylation and alkylation of the phenolic OH group in triazole 8 were unsuccessful; this was proved by theoretical calculations using the AM1 semi-empirical method.