2'-episalaprinol | 1080668-49-0

• 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
• 英文名称: 2'-episalaprinol
• 英文别名: epi-salaprinol；2'-epi-salaprinol
• CAS: 1080668-49-0
• 化学式: C₈H₁₆O₈S₂
• 分子量: 304.342
• InChiKey: WBUXSJSEIMPRAS-JKPORLPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.46
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  147.35
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2'-episalaprinol 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2'-epi-neosalaprinol
  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：

  (R)-2-(benzyloxy)-3-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophen-1-ium-1-yl)propyl sulfate 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以87%的产率得到2'-episalaprinol
  参考文献：
  名称：

  Synthesis and elucidation of absolute stereochemistry of salaprinol, another thiosugar sulfonium sulfate from the ayurvedic traditional medicine Salacia prinoides

  摘要：

  Synthesis and elucidation of absolute stereochemistry of salaprinol (3) isolated from the root and sterns of Salacia prinoides, which has been used for the treatment of diabetes in India, Sri Lanka, and Southeast Asia countries, is described. Compound 3 and its 2'-epimer, epi-salaprinol (epi-3) were synthesized via the coupling reaction of a cyclic sulfate, 2-O-benzylglycerol 1,3-cyclic sulfate (S), with a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (6), as the key reaction, and S configuration of the asymmetric center in the side chain of 3 was elucidated by the X-ray crystallographic analysis. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.08.010

文献信息

• Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors
  作者：Weijia Xie、Genzoh Tanabe、Junji Akaki、Toshio Morikawa、Kiyofumi Ninomiya、Toshie Minematsu、Masayuki Yoshikawa、Xiaoming Wu、Osamu Muraoka

  DOI：10.1016/j.bmc.2011.01.052

  日期：2011.3

  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.
• Synthesis and elucidation of absolute stereochemistry of salaprinol, another thiosugar sulfonium sulfate from the ayurvedic traditional medicine Salacia prinoides
  作者：Genzoh Tanabe、Mika Sakano、Toshie Minematsu、Hisashi Matusda、Masayuki Yoshikawa、Osamu Muraoka

  DOI：10.1016/j.tet.2008.08.010

  日期：2008.10

  Synthesis and elucidation of absolute stereochemistry of salaprinol (3) isolated from the root and sterns of Salacia prinoides, which has been used for the treatment of diabetes in India, Sri Lanka, and Southeast Asia countries, is described. Compound 3 and its 2'-epimer, epi-salaprinol (epi-3) were synthesized via the coupling reaction of a cyclic sulfate, 2-O-benzylglycerol 1,3-cyclic sulfate (S), with a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (6), as the key reaction, and S configuration of the asymmetric center in the side chain of 3 was elucidated by the X-ray crystallographic analysis. (C) 2008 Published by Elsevier Ltd.