(2R,3R,4R,6R)-3,4-di(benzyloxy)-2-benzyloxymethyl-6-ethylpiperidine | 605675-63-6

• 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,6R)-3,4-di(benzyloxy)-2-benzyloxymethyl-6-ethylpiperidine
• 英文别名: (2R,3R,4R,6R)-6-ethyl-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)piperidine
• CAS: 605675-63-6
• 化学式: C₂₉H₃₅NO₃
• 分子量: 445.602
• InChiKey: ZOHGPERMXJUIPO-CXDXLJMYSA-N

物化性质

• 沸点：
  556.1±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,6R)-3,4-di(benzyloxy)-2-benzyloxymethyl-6-ethylpiperidine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以88%的产率得到(2R,3R,4R,6R)-2-hydroxymethyl-6-ethylpiperidine-3,4-diol
  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 、 N-碘代丁二酰亚胺 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 sodium 、 乙二胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 61.0h， 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

文献信息

• Ring-opening reactions of iminosugar-derived aziridines: application to the general synthesis of α-1-C-substituted derivatives of fagomine
  作者：Jean-Yves Goujon、David Gueyrard、Philippe Compain、Olivier R. Martin、Naoki Asano

  DOI：10.1016/s0957-4166(03)00364-1

  日期：2003.7

  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.
• 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.