Acetic acid (2R,3R,4S,5R)-3,5-diacetoxy-2-acetoxymethyl-6-thioxo-piperidin-4-yl ester | 189128-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: Acetic acid (2R,3R,4S,5R)-3,5-diacetoxy-2-acetoxymethyl-6-thioxo-piperidin-4-yl ester
• CAS: 189128-82-3
• 化学式: C₁₄H₁₉NO₈S
• 分子量: 361.373
• InChiKey: CGLTUCDMZWNKPO-FVCCEPFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.36
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  117.23
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R)-3,5-diacetoxy-2-acetoxymethyl-6-thioxo-piperidin-4-yl ester 在 吡啶 、 甲醇 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  d-Glyconhydroximolactams strongly inhibit α-glycosidases

  摘要：

  It has been postulated that proton transfer to beta-glycosides by some retaining beta-glycosidases takes place in the plane of the pyranoside ring. It is now hypothesised that a similarly oriented catalytically active acidic group in alpha-glycosidases could interact with glyconolactone derivatives, provided that these are sufficiently basic to overcome the effect of a less favourable geometry by an energetically more favourable interaction. In keeping with this hypothesis, D-gluconolactone, D-gluconolactam, the tetrazole 3, and the hydroximolactone 5 are weak inhibitors of yeast alpha-glucosidase, while the hydroximolactam 6 (pK(a) = 4.8) is a mixed-type (alpha=2) strong inhibitor (K-i = 2.9 mu M). A Similar inhibition is observed for the arylcarbamoyl derivative 9, while the (methylthio)methyl derivative 10 inhibits more weakly and in a purely competitive fashion. The mannonhydroximolactam 11 strongly inhibits jack bean a-mannosidase (K-i=0.15 mu M), while the gluco analogue 6 inhibits about 80 times more weakly, illustrating the dependence upon configuration. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00320-5
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-5-amino-5-deoxy-D-glucono-1,5-lactam 在 劳森试剂 作用下， 反应 0.33h， 以80%的产率得到Acetic acid (2R,3R,4S,5R)-3,5-diacetoxy-2-acetoxymethyl-6-thioxo-piperidin-4-yl ester
  参考文献：
  名称：

  d-Glyconhydroximolactams strongly inhibit α-glycosidases

  摘要：

  It has been postulated that proton transfer to beta-glycosides by some retaining beta-glycosidases takes place in the plane of the pyranoside ring. It is now hypothesised that a similarly oriented catalytically active acidic group in alpha-glycosidases could interact with glyconolactone derivatives, provided that these are sufficiently basic to overcome the effect of a less favourable geometry by an energetically more favourable interaction. In keeping with this hypothesis, D-gluconolactone, D-gluconolactam, the tetrazole 3, and the hydroximolactone 5 are weak inhibitors of yeast alpha-glucosidase, while the hydroximolactam 6 (pK(a) = 4.8) is a mixed-type (alpha=2) strong inhibitor (K-i = 2.9 mu M). A Similar inhibition is observed for the arylcarbamoyl derivative 9, while the (methylthio)methyl derivative 10 inhibits more weakly and in a purely competitive fashion. The mannonhydroximolactam 11 strongly inhibits jack bean a-mannosidase (K-i=0.15 mu M), while the gluco analogue 6 inhibits about 80 times more weakly, illustrating the dependence upon configuration. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00320-5