(1R,2R,3R,5R)-3-amino-3-(aminomethyl)-5-(hydroxymethyl)cyclopentane-1,2-diol | 1045825-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3R,5R)-3-amino-3-(aminomethyl)-5-(hydroxymethyl)cyclopentane-1,2-diol
• CAS: 1045825-72-6
• 化学式: C₇H₁₆N₂O₃
• 分子量: 176.216
• InChiKey: CHIJWFIDAXJFDY-MVIOUDGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.62
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  112.73
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,5R)-3-amino-3-(aminomethyl)-5-(hydroxymethyl)cyclopentane-1,2-diol 、 二碳酸二叔丁酯 、 三氟乙酸 在 三乙胺 作用下， 以 甲醇 、 水 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (1R,2R,3R,5R)-3-amino-3-aminomethyl-5-hydroxymethyl-cyclopentane-1,2-diol trifluoroacetate
  参考文献：
  名称：

  Synthetic studies towards a new scaffold, spirobicycloimidazoline

  摘要：

  A new scaffold consisting of a carbocycle and a substituted imidazoline in an orthogonal arrangement was synthesized as a potential specific inhibitor of glycosidases. The spirobicycloimidazoline, (5R,6R,7R,8R)-8-(hydroxymethyl)-2-phenyl-1,3-diazaspiro[4.4]non-1-ene-6,7-diol, was synthesized from methyl 2-O-p-methoxybenzyl-3,4-di-O-benzyl-alpha/beta-D-gluco-6-enopyranoside via (1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-2-(4-methoxybenzyloxy)-5-vinyl-cyclopentanol. The ring contraction of the 6-enopyranoside in the presence of zirconocene equivalent ('Cp2Zr') reagent gave exclusively the corresponding cyclopentanol without cleavage of the PMB protecting group. In the course of the study, a new alpha-mannosidase inhibitor, (1R,2R,3R,5R)-5-amino-3-hydroxymethyl-cyclopentane-1,2-diol, was also discovered. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.025
• 作为产物：
  描述：

  (1R,2R,3R,5R)-3-azido-3-benzylaminomethyl-1,2-bis(benzyloxy)-5-trityloxymethyl-cyclopentane 在 palladium hydroxide - carbon 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 20.0h， 生成 (1R,2R,3R,5R)-3-amino-3-(aminomethyl)-5-(hydroxymethyl)cyclopentane-1,2-diol
  参考文献：
  名称：

  Synthetic studies towards a new scaffold, spirobicycloimidazoline

  摘要：

  A new scaffold consisting of a carbocycle and a substituted imidazoline in an orthogonal arrangement was synthesized as a potential specific inhibitor of glycosidases. The spirobicycloimidazoline, (5R,6R,7R,8R)-8-(hydroxymethyl)-2-phenyl-1,3-diazaspiro[4.4]non-1-ene-6,7-diol, was synthesized from methyl 2-O-p-methoxybenzyl-3,4-di-O-benzyl-alpha/beta-D-gluco-6-enopyranoside via (1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-2-(4-methoxybenzyloxy)-5-vinyl-cyclopentanol. The ring contraction of the 6-enopyranoside in the presence of zirconocene equivalent ('Cp2Zr') reagent gave exclusively the corresponding cyclopentanol without cleavage of the PMB protecting group. In the course of the study, a new alpha-mannosidase inhibitor, (1R,2R,3R,5R)-5-amino-3-hydroxymethyl-cyclopentane-1,2-diol, was also discovered. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.025