[(6R,7R,8S,8aS)-7,8-diacetyloxy-3,5,6,7,8,8a-hexahydro-2H-[1,3]thiazolo[3,2-a]pyridin-6-yl] acetate | 143308-44-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(6R,7R,8S,8aS)-7,8-diacetyloxy-3,5,6,7,8,8a-hexahydro-2H-[1,3]thiazolo[3,2-a]pyridin-6-yl] acetate
• CAS: 143308-44-5；143392-98-7
• 化学式: C₁₃H₁₉NO₆S
• 分子量: 317.363
• InChiKey: GKTJBJWJHKCUTF-NDBYEHHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(6R,7R,8S,8aS)-7,8-diacetyloxy-3,5,6,7,8,8a-hexahydro-2H-[1,3]thiazolo[3,2-a]pyridin-6-yl] acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (6R,7R,8S)-Hexahydro-thiazolo[3,2-a]pyridine-6,7,8-triol
  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：

  O⁵-(toluene-4-sulfonyl)-D-arabinose diethyl dithioacetal 在 吡啶 、 potassium carbonate 、 sodium sulfate 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 93.0h， 生成 [(6R,7R,8S,8aS)-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