1-deoxy-1-isothiocyanato-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose | 1184960-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-1-isothiocyanato-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose
• CAS: 1184960-30-2
• 化学式: C₁₃H₁₉NO₅S
• 分子量: 301.364
• InChiKey: REPZJPYQCKTXQQ-WJZNIJOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  58.51
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-isothiocyanato-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose 、 邻氨基苯甲酸甲酯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以73%的产率得到N-(1-deoxy-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranosyl)-N'-(2-methoxycarbonylphenyl)thiourea
  参考文献：
  名称：

  Modular access to heterocycles: methyl 3-aminobenzo[b]thiophene-2-carboxylate–thiourea linkage or pyrimidine-4-one-2-thione formation

  摘要：

  Modular conditions for the formation of thioureas or pyrimidine-4-one-2-thiones connected to the benzo[b]thiophene, benzene and indole structures were performed. A benzo[b]thiophene isothiocyanate derivative was used as a model to study the condensation with simple aromatic amines and amino-L-sorbose derivative. The construction of pyrimidine-4-one-2-thiones using basic conditions afforded efficiently new heterocyclic aromatics, which were further transformed using the alkylated sulfur as a leaving group in palladium-catalyzed cross-coupling reactions.

  DOI：

  10.1007/s00706-008-0030-5
• 作为产物：
  描述：

  二硫化碳 、 1-deoxy-1-azido-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose 在 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 32.0h， 以89%的产率得到1-deoxy-1-isothiocyanato-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose
  参考文献：
  名称：

  Modular access to heterocycles: methyl 3-aminobenzo[b]thiophene-2-carboxylate–thiourea linkage or pyrimidine-4-one-2-thione formation

  摘要：

  Modular conditions for the formation of thioureas or pyrimidine-4-one-2-thiones connected to the benzo[b]thiophene, benzene and indole structures were performed. A benzo[b]thiophene isothiocyanate derivative was used as a model to study the condensation with simple aromatic amines and amino-L-sorbose derivative. The construction of pyrimidine-4-one-2-thiones using basic conditions afforded efficiently new heterocyclic aromatics, which were further transformed using the alkylated sulfur as a leaving group in palladium-catalyzed cross-coupling reactions.

  DOI：

  10.1007/s00706-008-0030-5