(1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-hex-5-enylamine | 605675-50-1

• 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: (1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-hex-5-enylamine
• CAS: 605675-50-1
• 化学式: C₂₈H₃₃NO₃
• 分子量: 431.575
• InChiKey: BBCJOZQOAJFFBY-JCYYIGJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  32.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-hex-5-enylamine 在 N-碘代丁二酰亚胺 、 lithium perchlorate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.0h， 生成 4,5,7-tri-O-benzyl-1,2,3,6-tetradeoxy-2,6-imino-1-morpholino-D-manno-heptitol
  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：

  (2S,3R,4R)-1,3,4-Tris-benzyloxy-hept-6-en-2-ol 在 偶氮二甲酸二异丙酯 、 乙二胺 、 三苯基膦 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 21.0h， 生成 (1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-hex-5-enylamine
  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

文献信息

• Chemistry of Imino Glycals: Preparation and Application to the Synthesis of (+)-Fagomine
  作者：Jérôme Désiré、Paul J. Dransfield、Paul M. Gore、Michael Shipman

  DOI：10.1055/s-2001-16039

  日期：——

  The synthesis of imino glucal 2 from tri-O-benzyl-d-glucal in 8 steps is described. This novel imino sugar building block is further converted into (+)-fagomine by a two-step hydrogenation sequence.

  本文介绍了通过 8 个步骤从三-O-苄基-d-葡萄糖醛合成亚氨基葡萄糖醛 2 的过程。这种新颖的亚氨基糖结构单元通过两步氢化程序进一步转化为 (+)- 法戈明。