methyl 2-deoxy-3,4-O-isopropylidene-5-[(R)-methyl episulfonium]-1-thio-D-erythro-pent-1-enopyranoside trifluoromethanesulfonate | 1196988-82-5

• 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: methyl 2-deoxy-3,4-O-isopropylidene-5-[(R)-methyl episulfonium]-1-thio-D-erythro-pent-1-enopyranoside trifluoromethanesulfonate
• CAS: 1196988-82-5
• 化学式: CF₃O₃S*C₁₀H₁₇O₂S₂
• 分子量: 382.446
• InChiKey: PGWQRDBHTJTDIQ-QMOWBMIFSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  methyl 2-deoxy-3,4-O-isopropylidene-5-[(R)-methyl episulfonium]-1-thio-D-erythro-pent-1-enopyranoside trifluoromethanesulfonate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到methyl 2-deoxy-5-[methylsulfonium]-1-thio-D-erythropent-1-enopyranoside 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 、 2-deoxy-3,4-O-isopropylidene-D-erythro-pent-1-enose dimethyldithioacetal 在 2,6-di-tert-butyl-4-methylpyridine 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到methyl 2-deoxy-3,4-O-isopropylidene-5-[(R)-methyl episulfonium]-1-thio-D-erythro-pent-1-enopyranoside 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