莎拉西娅根茎提取物 | 200399-47-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 中文名称: 莎拉西娅根茎提取物
• 英文名称: salacinol
• 英文别名: [(2S,3S)-4-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)thiolan-1-ium-1-yl]-1,3-dihydroxybutan-2-yl] sulfate
• CAS: 200399-47-9
• 化学式: C₉H₁₈O₉S₂
• 分子量: 334.369
• InChiKey: SOWRVDSZMRPKRG-XESHOGEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  177
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 莎拉西娅根茎提取物
  参考文献：
  名称：

  Synthesis of salacinol

  摘要：

  Salacinol, a new type of alpha-glucosidase inhibitor discovered from the antidiabetic herb, was synthesized for the first time. Under the strategy that salacinol would be synthesized by the coupling reaction between 1,4-epithio-D-arabinitol and the cyclic sulfate of an erythritol derivative, the model coupling reactions between tetrahydrothiophene and versatile cyclic sulfate derivatives were undertaken. These experiments indicated that the 1,3-diol of the cyclic sulfate should be protected with the isopropylidene group, otherwise, even the benzylidene-protected cyclic sulfate decomposed during the reaction. Thus, the salacinol was synthesized using the cyclic sulfate of 1,3-O-isopypropylidene-D-erythritol. The resulting coupling product was deisopropylidenated to afford salacinol. A diastereomer of salacinol was also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01129-1