(1'R,2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>-2-<1',2'-dihydroxyethyl>pyrrolidine | 173142-28-4

• 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: (1'R,2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>-2-<1',2'-dihydroxyethyl>pyrrolidine
• 英文别名: (2R,3R,4R,5R,1'S)-5-benzyloxymethyl-3,4-dibenzyloxy-2-(1',2'-dihydroxy)ethyl-pyrrolidine；(1S)-1-[(2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidin-2-yl]ethane-1,2-diol
• CAS: 173142-28-4
• 化学式: C₂₈H₃₃NO₅
• 分子量: 463.574
• InChiKey: CIKICCHRCOXGCC-JQPIIJRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1'R,2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>-2-<1',2'-dihydroxyethyl>pyrrolidine 在 palladium on activated charcoal sodium azide 、 氢气 、 三乙胺 、 三氟乙酸 、 potassium iodide 、 silver(l) oxide 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 71.0h， 生成 (1'R,2R,3R,4R,5R)-2-<2-acetamido-1-(benzyloxy)ethyl>-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine
  参考文献：
  名称：

  A Versatile Synthetic Strategy for the Preparation and Discovery of New Iminocyclitols as Inhibitors of Glycosidases

  摘要：

  A series of iminocyclitols was prepared using a versatile synthetic strategy, and their inhibition of glycosidases was evaluated using capillary electrophoresis. The study has demonstrated that remarkable specificities in enzyme inhibition can be achieved with small modifications on the aglycon side chain and the ring nitrogen. Among the compounds synthesized, (2R,3R,4R,5R)-N-methyl-2-(acetamidomethyl)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidine was found to be very potent; against beta-N-acetylhexosaminidase P with the K-i value of 80 nM.

  DOI：

  10.1021/jo9902446
• 作为产物：
  描述：

  (2R,3S,4S,5R,6R)-6-azido-2,3-epoxy-4,5,7-tris(benzyloxy)-2(E)-hepten-1-ol 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以91%的产率得到(1'R,2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>-2-<1',2'-dihydroxyethyl>pyrrolidine
  参考文献：
  名称：

  A Versatile Synthetic Strategy for the Preparation and Discovery of New Iminocyclitols as Inhibitors of Glycosidases

  摘要：

  A series of iminocyclitols was prepared using a versatile synthetic strategy, and their inhibition of glycosidases was evaluated using capillary electrophoresis. The study has demonstrated that remarkable specificities in enzyme inhibition can be achieved with small modifications on the aglycon side chain and the ring nitrogen. Among the compounds synthesized, (2R,3R,4R,5R)-N-methyl-2-(acetamidomethyl)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidine was found to be very potent; against beta-N-acetylhexosaminidase P with the K-i value of 80 nM.

  DOI：

  10.1021/jo9902446

文献信息

• Iminocyclitol inhibitors of hexoaminidase and glycosidase
  申请人：The Scripps Research Institute

  公开号：US06774140B1

  公开（公告）日：2004-08-10

  Designed iminocylitols that have potent inhibition activity with respect to hexominidases and glycosides are disclosed.

  披露了设计的亚氨基糖醇，它们对己糖苷酶和苷具有强大的抑制活性。
• A Versatile Synthetic Strategy for the Preparation and Discovery of New Iminocyclitols as Inhibitors of Glycosidases
  作者：Maki Takebayashi、Sayoko Hiranuma、Yoshimi Kanie、Tetsuya Kajimoto、Osamu Kanie、Chi-Huey Wong

  DOI：10.1021/jo9902446

  日期：1999.7.1

  A series of iminocyclitols was prepared using a versatile synthetic strategy, and their inhibition of glycosidases was evaluated using capillary electrophoresis. The study has demonstrated that remarkable specificities in enzyme inhibition can be achieved with small modifications on the aglycon side chain and the ring nitrogen. Among the compounds synthesized, (2R,3R,4R,5R)-N-methyl-2-(acetamidomethyl)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidine was found to be very potent; against beta-N-acetylhexosaminidase P with the K-i value of 80 nM.