3,5-di-O-acetyl-6-deoxy-1,2-O-isopropylidene-6-isothiocyanate-α-D-glucofuranose | 1071856-68-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-di-O-acetyl-6-deoxy-1,2-O-isopropylidene-6-isothiocyanate-α-D-glucofuranose
• CAS: 1071856-68-2
• 化学式: C₁₄H₁₉NO₇S
• 分子量: 345.373
• InChiKey: SBCJTADTNUVVSX-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  92.65
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3,5-di-O-acetyl-6-deoxy-1,2-O-isopropylidene-6-isothiocyanate-α-D-glucofuranose 、 对溴苯甲酰肼 以 四氢呋喃 为溶剂， 反应 2.0h， 以100%的产率得到3,5-di-O-acetyl-6-deoxy-1,2-isopropylidene-6-[(p-bromobenzohydrazinecarbothionyl)amino]-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis and antiviral activity of azoles obtained from carbohydrates

  摘要：

  Herein we describe the synthesis of 1,2,4-triazolyl-3-thione; 1,3,4-oxadiazole, and imidazo[2,1-b]thiazole derivatives from carbohydrates. The antiviral activity of these compounds was tested against Dengue and Junin virus (the etiological agent of Argentine hemorrhagic fever). The 3-(p-bromobenzoyl)-5-(1,2-O-isopropylidene-3-O-methyl-alpha-D-xylofuranos-5-ulos-5-yl)imidazo[2,1-b]thiazole was able to inhibit the replication of both viruses in Vero cells at concentration significantly lower than the CC50. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.06.028
• 作为产物：
  描述：

  二硫化碳 、 6-叠氮基-6-脱氧-1,2-O-(1-甲基乙亚基)-alpha-D-呋喃葡萄糖 、 乙酸酐 在 吡啶 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 以84.9%的产率得到3,5-di-O-acetyl-6-deoxy-1,2-O-isopropylidene-6-isothiocyanate-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis and antiviral activity of azoles obtained from carbohydrates

  摘要：

  Herein we describe the synthesis of 1,2,4-triazolyl-3-thione; 1,3,4-oxadiazole, and imidazo[2,1-b]thiazole derivatives from carbohydrates. The antiviral activity of these compounds was tested against Dengue and Junin virus (the etiological agent of Argentine hemorrhagic fever). The 3-(p-bromobenzoyl)-5-(1,2-O-isopropylidene-3-O-methyl-alpha-D-xylofuranos-5-ulos-5-yl)imidazo[2,1-b]thiazole was able to inhibit the replication of both viruses in Vero cells at concentration significantly lower than the CC50. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.06.028