1,4-bis(5-thioxo-1,3,4-thiadiazol-2-yl)galacto-tetritol | 883868-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4-bis(5-thioxo-1,3,4-thiadiazol-2-yl)galacto-tetritol
• 英文别名: 5-[(1S,2R,3S,4R)-1,2,3,4-tetrahydroxy-4-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)butyl]-3H-1,3,4-thiadiazole-2-thione
• CAS: 883868-08-4
• 化学式: C₈H₁₀N₄O₄S₄
• 分子量: 354.456
• InChiKey: MXULPTXHELXXLN-DUHBMQHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  245
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,4-bis(5-thioxo-1,3,4-thiadiazol-2-yl)galacto-tetritol 、 乙酸酐 在 吡啶 作用下， 反应 72.0h， 以77%的产率得到1,2,3,4-tetra-O-acetyl-1,4-bis(4-acetyl-5-thioxo-1,3,4-thiadiazolin-2-yl)galacto-tetritol
  参考文献：
  名称：

  Utilization of Dipotassium Salt of Galactaric Acid Bis(Hydrazidocarbodithioic Acid) As a Synthone for Double-Headed 1,3,4-Thiadiazoline, 1,3,4-Oxadiazoline and 1,2,4-Triazoline Acyclo C-Nucleosides

  摘要：

  Condensation of galactaric acid bis hydrazide (1) with carbon disulfide in the presence of ethanolic potassium hydroxide gave the dipotassium salt of galactaric acid bis (hydrazidocarbodithioic acid) (2). Heterocyclization of the key compound 2 produced three different types of double headed acyclo C-nucleosides: acid-catalyzed dehydrative cyclization afforded the 5-thioxo-1,3,4-thiadiazoline 3, base-catalyzed dehydrosulfurative cyclization gave the 5-thioxo-1,3,4-oxadiazoline 5, and condensative cyclization with concomitant dehydrosulfuration and dehydration with different nitrogen nucleophiles yielded the 5-thioxo-1,2,4-triazolines 7 and 9a, b.Acetylation of the prepared acyclo C-nucleosides 3, 5, 7 and 9a, b with acetic anhydride in the presence of pyridine at ambient temperature caused acetylation of the sugar hydroxyls as well as heterocyclo imino protons to give the tetra-O-acetates 4, 6, and 10a, b, respectively. Representative members of the prepared compounds were tested for antimicrobial activity.

  DOI：

  10.1080/104265090888397
• 作为产物：
  描述：

  galactaric acid bishydrazide 在 氢氧化钾 、 硫酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 26.0h， 生成 1,4-bis(5-thioxo-1,3,4-thiadiazol-2-yl)galacto-tetritol
  参考文献：
  名称：

  Utilization of Dipotassium Salt of Galactaric Acid Bis(Hydrazidocarbodithioic Acid) As a Synthone for Double-Headed 1,3,4-Thiadiazoline, 1,3,4-Oxadiazoline and 1,2,4-Triazoline Acyclo C-Nucleosides

  摘要：

  Condensation of galactaric acid bis hydrazide (1) with carbon disulfide in the presence of ethanolic potassium hydroxide gave the dipotassium salt of galactaric acid bis (hydrazidocarbodithioic acid) (2). Heterocyclization of the key compound 2 produced three different types of double headed acyclo C-nucleosides: acid-catalyzed dehydrative cyclization afforded the 5-thioxo-1,3,4-thiadiazoline 3, base-catalyzed dehydrosulfurative cyclization gave the 5-thioxo-1,3,4-oxadiazoline 5, and condensative cyclization with concomitant dehydrosulfuration and dehydration with different nitrogen nucleophiles yielded the 5-thioxo-1,2,4-triazolines 7 and 9a, b.Acetylation of the prepared acyclo C-nucleosides 3, 5, 7 and 9a, b with acetic anhydride in the presence of pyridine at ambient temperature caused acetylation of the sugar hydroxyls as well as heterocyclo imino protons to give the tetra-O-acetates 4, 6, and 10a, b, respectively. Representative members of the prepared compounds were tested for antimicrobial activity.

  DOI：

  10.1080/104265090888397