4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-D-manno-heptitol | 605675-61-4

• 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: 4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-D-manno-heptitol
• 英文别名: dibenzyl [(2S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)piperidin-2-yl]methyl phosphate
• CAS: 605675-61-4
• 化学式: C₄₂H₄₆NO₇P
• 分子量: 707.803
• InChiKey: AREWMRLKKMDJQF-CVGILMMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  51
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-D-manno-heptitol 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 以85%的产率得到2,3,6-trideoxy-2,6-imino-D-manno-heptitol-1-phosphate
  参考文献：
  名称：

  General synthesis and biological evaluation of α-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-α-C-glycosides)

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2004.12.043
• 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 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 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 77.0h， 生成 4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-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

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.