(1'R,2R,3R,4R,5R)-N-butyloxycarbonyl-2-<2-azido-1-(benzyloxy)ethyl>-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine | 231618-99-8

• 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,3R,4R,5R)-N-butyloxycarbonyl-2-<2-azido-1-(benzyloxy)ethyl>-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine
• 英文别名: (1'R,2R,3R,4R,5R)-N-butyloxycarbonyl-[2-(2'-azido-1'-benzyloxy-ethyl)-3,4-dibenzyloxy-5-benzyloxymethyl]-prrolidine；tert-butyl (2R,3R,4R,5R)-2-[(1R)-2-azido-1-phenylmethoxyethyl]-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidine-1-carboxylate
• CAS: 231618-99-8
• 化学式: C₄₀H₄₆N₄O₆
• 分子量: 678.828
• InChiKey: VWRZJEQOVJUUSU-OHTWKVNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  50
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1'R,2R,3R,4R,5R)-N-butyloxycarbonyl-2-<2-azido-1-(benzyloxy)ethyl>-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 3.0h， 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 sodium azide 、 三乙胺 、 三苯基膦 、 potassium iodide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 116.0h， 生成 (1'R,2R,3R,4R,5R)-N-butyloxycarbonyl-2-<2-azido-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

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。
• From Lianas to Glycobiology Tools: Twenty-Five Years of 2,5-Dideoxy-2,5-imino-D-mannitol
  作者：Tanja M. Wrodnigg

  DOI：10.1007/s007060200018

  日期：2002.4.1

  2,5-Dideoxy-2,5-imino-D-mannitol (DMDP) has been isolated from several natural sources. Many synthetic approaches are available, and many derivatives have been synthesized and their biological activities have been investigated. An overview on isolation, syntheses, and biological data of DMDP as well as some closely related compounds will be given in this review.
• 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.