Acetic acid (R)-2-methanesulfonyloxy-1-{(4S,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl ester | 914982-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Acetic acid (R)-2-methanesulfonyloxy-1-{(4S,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl ester
• CAS: 914982-65-3
• 化学式: C₂₀H₃₁NO₁₂S₃
• 分子量: 573.664
• InChiKey: HCLBOQRCHGMECQ-WJFTUGDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.05
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  177.67
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (R)-2-methanesulfonyloxy-1-{(4S,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以88%的产率得到(S)-2-((4R,5S)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-yl)-1-tosylaziridine
  参考文献：
  名称：

  Synthesis of enantiopure bis-aziridines, bis-epoxides, and aziridino-epoxides from d-mannitol

  摘要：

  A practical synthesis of enantiopure bis-aziridines 11 and 15, bis-epoxides 12 and 17, and aziridino-epoxides 27 and 30 is reported using inexpensive D-mannitol as the starting material. The key transformation involves the reductive cleavage of bis-benzylidene acetal 3 to form dimesylate 4, which was further converted to monoazides and diazides followed by reduction, mesylation, and cyclization to furnish the required compounds in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.035
• 作为产物：
  描述：

  在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 30.0h， 生成 Acetic acid (R)-2-methanesulfonyloxy-1-{(4S,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl ester
  参考文献：
  名称：

  Synthesis of enantiopure bis-aziridines, bis-epoxides, and aziridino-epoxides from d-mannitol

  摘要：

  A practical synthesis of enantiopure bis-aziridines 11 and 15, bis-epoxides 12 and 17, and aziridino-epoxides 27 and 30 is reported using inexpensive D-mannitol as the starting material. The key transformation involves the reductive cleavage of bis-benzylidene acetal 3 to form dimesylate 4, which was further converted to monoazides and diazides followed by reduction, mesylation, and cyclization to furnish the required compounds in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.035