2-((1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-hex-5-enyl)-isoindole-1,3-dione | 850190-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-((1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-hex-5-enyl)-isoindole-1,3-dione
• CAS: 850190-26-0
• 化学式: C₃₆H₃₅NO₅
• 分子量: 561.678
• InChiKey: ATXMJLOMUUUFIW-CKOYEXALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-((1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-hex-5-enyl)-isoindole-1,3-dione 在 N-碘代丁二酰亚胺 、 乙二胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2R,3R,4R,6R)-3,4-di(benzyloxy)-2-benzyloxymethyl-6-ethylpiperidine
  参考文献：
  名称：

  Ring-opening reactions of iminosugar-derived aziridines: application to the general synthesis of α-1-C-substituted derivatives of fagomine

  摘要：

  A general approach to alpha-l-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides) by ring-opening reactions of an aziridine with various heteroatomic nucleophiles, including thiol, amine, alcohol, carboxylate and phosphate, is reported. The nine-step reaction sequence proceeded in an overall yield of 14-28% from tri-O-benzyl-D-glucal. In the course of this study, the synthesis of alpha-1-C-ethyl-fagomine as well as of 1,N-anhydro derivatives of fagomine has been achieved for the first time. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00364-1
• 作为产物：
  描述：

  3,4,6-三-氧-苄基-2-脱氧-D-吡喃葡萄糖 在 甲醇 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 sodium 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 49.0h， 生成 2-((1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-hex-5-enyl)-isoindole-1,3-dione
  参考文献：
  名称：

  Ring-opening reactions of iminosugar-derived aziridines: application to the general synthesis of α-1-C-substituted derivatives of fagomine

  摘要：

  A general approach to alpha-l-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides) by ring-opening reactions of an aziridine with various heteroatomic nucleophiles, including thiol, amine, alcohol, carboxylate and phosphate, is reported. The nine-step reaction sequence proceeded in an overall yield of 14-28% from tri-O-benzyl-D-glucal. In the course of this study, the synthesis of alpha-1-C-ethyl-fagomine as well as of 1,N-anhydro derivatives of fagomine has been achieved for the first time. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00364-1