1,4-dideoxy-1,4-{(R)-[(2S,3R,4R,5S)-2,3,4,5,6-pentahydroxyhexyl]episulfoniumylidene}-D-arabinitol chloride | 1300116-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-dideoxy-1,4-{(R)-[(2S,3R,4R,5S)-2,3,4,5,6-pentahydroxyhexyl]episulfoniumylidene}-D-arabinitol chloride
• 英文别名: 3'-epi-neoponkoranol
• CAS: 1300116-28-2
• 化学式: C₁₁H₂₃O₈S*Cl
• 分子量: 350.818
• InChiKey: ATEIRTWZLSRKMU-AEJADQTDSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -7.86
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  161.84
• 氢给体数：
  8.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  1,2:3,4-di-O-isopropylidene-6-O-trifluoromethanesulfonyl-α-D-galactopyranose 在 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 18.33h， 生成 1,4-dideoxy-1,4-{(R)-[(2S,3R,4R,5S)-2,3,4,5,6-pentahydroxyhexyl]episulfoniumylidene}-D-arabinitol chloride
  参考文献：
  名称：

  Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors

  摘要：

  Two hitherto missing members of sulfonium salts family in Salacia genus plants as a new class of a-glucosidase inhibitors, neoponkoranol (7) and neosalaprinol (8), were isolated from the water extracts, and their structures were unambiguously identified. For further SAR studies on this series of sulfonium salts, several epimers of 7 and 8 were synthesized, and their inhibitory activities against rat small intestinal alpha-glucosidases were evaluated. Among them, 3'-epimer of 7 was found most potent in this class of molecules, and revealed as potent as currently used antidiabetics, voglibose and acarbose. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.052