2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-[(S)-(1,2:3,4-di-O-isopropylidene-6-deoxy-α-D-galactopyranos-6-yl)episulfoniumylidene]-D-arabinitol trifluoromethanesulfonate | 1300116-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-[(S)-(1,2:3,4-di-O-isopropylidene-6-deoxy-α-D-galactopyranos-6-yl)episulfoniumylidene]-D-arabinitol trifluoromethanesulfonate
• CAS: 1300116-19-1
• 化学式: CF₃O₃S*C₃₈H₄₇O₈S
• 分子量: 812.923
• InChiKey: CPMRZWOHYJOXMZ-HAYYMPBDSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  55.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  131.04
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-[(S)-(1,2:3,4-di-O-isopropylidene-6-deoxy-α-D-galactopyranos-6-yl)episulfoniumylidene]-D-arabinitol trifluoromethanesulfonate 在 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 、 sodium tetrahydroborate 、 水 作用下， 以 1,4-二氧六环 、 水 、 甲醇 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 3.33h， 以50%的产率得到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
• 作为产物：
  描述：

  双丙酮半乳糖 在 2,6-二甲基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.58h， 生成 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-[(S)-(1,2:3,4-di-O-isopropylidene-6-deoxy-α-D-galactopyranos-6-yl)episulfoniumylidene]-D-arabinitol trifluoromethanesulfonate
  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