(2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-iodomethyl-piperidine | 850190-27-1

• 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: (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-iodomethyl-piperidine
• CAS: 850190-27-1
• 化学式: C₂₈H₃₂INO₃
• 分子量: 557.471
• InChiKey: QTMPNULBIQVGLJ-RFBUSEEYSA-N

物化性质

• 沸点：
  602.8±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  39.72
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-iodomethyl-piperidine 在 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 、 乙腈 为溶剂， 反应 8.0h， 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：

  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 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-iodomethyl-piperidine
  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

• General synthesis and biological evaluation of α-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-α-C-glycosides)
  作者：Jean-Yves Goujon、David Gueyrard、Philippe Compain、Olivier R. Martin、Kyoko Ikeda、Atsushi Kato、Naoki Asano

  DOI：10.1016/j.bmc.2004.12.043

  日期：2005.3

  A general synthesis of alpha-1-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 described. The nine-step reaction sequence proceeded in an overall yield of 14-28% from tri-O-benzyl-D-glucal. Biological evaluation of alpha-1-C-substituted derivatives of fagomine, of the 2-deoxy analog of alpha-homonojirimycin 19 and its 1,N-anhydro derivative 22 as glycosidase inhibitors is reported. The glycosyl phosphate mimetic 15k was found to display no inhibitory activity towards glycogen phosphorylase b and phosphoglucomutase. (c) 2005 Elsevier Ltd. All rights reserved.