(5R,7S,8S) 7,8-isopropylidenedioxy-2,3,4,6,7,8-hexahydrothiopyrano[1,2-a][1,3]dithiin-5-ium trifluoromethanesulfonate | 1196988-84-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (5R,7S,8S) 7,8-isopropylidenedioxy-2,3,4,6,7,8-hexahydrothiopyrano[1,2-a][1,3]dithiin-5-ium trifluoromethanesulfonate
• CAS: 1196988-84-7
• 化学式: CF₃O₃S*C₁₁H₁₇O₂S₂
• 分子量: 394.457
• InChiKey: NKGBMAVLRCWFPR-FVCDVKBJSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  75.66
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (5R,7S,8S) 7,8-isopropylidenedioxy-2,3,4,6,7,8-hexahydrothiopyrano[1,2-a][1,3]dithiin-5-ium trifluoromethanesulfonate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(5R,7S,8S)-7,8-dihydroxy-2,3,4,6,7,8-hexahydrothiopyrano-[1,2-a][1,3]dithiin-5-ium trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of d- and l-erythro 1,5-dithiopent-1-enopyranoside sulfonium salts and their evaluation as glycosidase inhibitors

  摘要：

  A series of sulfonium salts derived from 1,5-dithiopent-1-enopyranosides was prepared in a three-step sequence from protected D- and L-erythrofuranoses. The key step is the nucleophilic displacement of a leaving group by a sulfur atom of carbohydrate-derived ketene dithioacetals. Such compounds were assayed for their properties as glycosidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.033
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (4S,5R)-4-(1,3-dithian-2-ylidenemethyl)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 在 2,6-di-tert-butyl-4-methylpyridine 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到(5R,7S,8S) 7,8-isopropylidenedioxy-2,3,4,6,7,8-hexahydrothiopyrano[1,2-a][1,3]dithiin-5-ium trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of d- and l-erythro 1,5-dithiopent-1-enopyranoside sulfonium salts and their evaluation as glycosidase inhibitors

  摘要：

  A series of sulfonium salts derived from 1,5-dithiopent-1-enopyranosides was prepared in a three-step sequence from protected D- and L-erythrofuranoses. The key step is the nucleophilic displacement of a leaving group by a sulfur atom of carbohydrate-derived ketene dithioacetals. Such compounds were assayed for their properties as glycosidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.033