2-(D-arabino-1,2,3,4-tetrahydroxybutyl)thiazolidine HCl salt | 143392-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(D-arabino-1,2,3,4-tetrahydroxybutyl)thiazolidine HCl salt
• CAS: 143392-95-4；143392-96-5
• 化学式: C₇H₁₅NO₄S*ClH
• 分子量: 245.727
• InChiKey: GRWSTMDQMMULMI-HVNVWVNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.85
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  92.95
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(D-arabino-1,2,3,4-tetrahydroxybutyl)thiazolidine HCl salt 在 吡啶 、 四氯化碳 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 192.0h， 生成 [(6R,7R,8S,8aR)-7,8-diacetyloxy-3,5,6,7,8,8a-hexahydro-2H-[1,3]thiazolo[3,2-a]pyridin-6-yl] acetate
  参考文献：
  名称：

  Synthesis of (6R,7R,8S,8aR)-6,7,8-trihydroxyperhydro[1,3]thiazolo[3,2-a]pyridine and its 8aS-epimer. Novel, biologically active analogs of castanospermine

  摘要：

  Concise syntheses of the title compounds 4a and 4b have been achieved from D-(-)-arabinose. In the first route the dithioacetal 9 was converted via the tosylate 10 to the hemiacetal 11 which was reacted with amino-ethanethiol.HCl to give a mixture of compounds 4. Alternatively, the thiazolidines 6 were cyclized (using Ph3P, CCl4, Et3N) to give 4a,b in a two-step approach without recourse to protecting groups. Castanospermine analogs 4 show in vitro activity against HIV at muM concentrations.

  DOI：

  10.1021/jo00047a018
• 作为产物：
  描述：

  D-阿拉伯糖 、 半胱胺盐酸盐 在 吡啶 作用下， 反应 20.0h， 以77.5%的产率得到2-(D-arabino-1,2,3,4-tetrahydroxybutyl)thiazolidine HCl salt
  参考文献：
  名称：

  Synthesis of (6R,7R,8S,8aR)-6,7,8-trihydroxyperhydro[1,3]thiazolo[3,2-a]pyridine and its 8aS-epimer. Novel, biologically active analogs of castanospermine

  摘要：

  Concise syntheses of the title compounds 4a and 4b have been achieved from D-(-)-arabinose. In the first route the dithioacetal 9 was converted via the tosylate 10 to the hemiacetal 11 which was reacted with amino-ethanethiol.HCl to give a mixture of compounds 4. Alternatively, the thiazolidines 6 were cyclized (using Ph3P, CCl4, Et3N) to give 4a,b in a two-step approach without recourse to protecting groups. Castanospermine analogs 4 show in vitro activity against HIV at muM concentrations.

  DOI：

  10.1021/jo00047a018