2-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl-thio)benzimidazole | 1246768-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl-thio)benzimidazole
• 英文别名: 2-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosylthio)benzimidazole
• CAS: 1246768-83-1
• 化学式: C₂₁H₂₅N₃O₈S
• 分子量: 479.511
• InChiKey: FBBHPQKZAITEOK-WAPOTWQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  145.91
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  邻苯二胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.0h， 生成 2-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl-thio)benzimidazole
  参考文献：
  名称：

  Revisit to the Reaction ofO-Phenylene Diamine with Thiosemicarbazide to Give Benzimidazole-2-Thione Rather than Benzotriazine-2-Thione and its Glycosylation

  摘要：

  Reaction of o-phenylene diamine with thiosemicarbazide did not give benzotriazine-2-thione 2 as reported, although the product was found to be benzimidazole-2-thione 3. Glycosylation of 3 with acetobromo sugars 4a-4b gave the respective thioglycosides 7a-7d in addition to minor products of the nucleosides 8a and 8b, in the case of the gluco- and galacto-analogs, respectively. The regioselectivity of glycosylation reaction has been investigated.

  DOI：

  10.1080/15257770.2010.501777

文献信息

• Specific Features of Phase Transfer Catalytic Glycosylation of 2-Mercaptobenzimidazole
  作者：T. A. Chupakhina、V. O. Kur’yanov

  DOI：10.1134/s1068162020060047

  日期：2020.11

  Abstract The reaction of 2-acetamido-3,4,6-tri- O -acetyl-2-deoxy-α-D-glucopyranosyl chloride with 2‑mercaptobenzimidazole under conditions of the phase transfer catalysis was studied and specific features of the phase transfer process were evaluated. It was found that the corresponding N - and S -β-D-glucosaminides were the major glucosaminylation products. Glucosaminylation of 2-mercaptobenzimidazole

  摘要 研究了2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-α-D-吡喃葡萄糖基氯与2-巯基苯并咪唑在相转移催化条件下的反应及其相转移的特点。过程进行了评价。发现相应的N-和S-β-D-氨基葡萄糖是主要的氨基葡萄糖化产物。2-巯基苯并咪唑在无水二氯甲烷-氢化钠相转移催化体系中的氨基葡萄糖化显示出区域特异性。合成化合物的结构使用 1 H NMR 光谱和质谱进行表征。