(2R,3S,4S,5R,6R)-6-azido-2,3-epoxy-4,5,7-tris(benzyloxy)-2(E)-hepten-1-ol | 231619-09-3

• 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,3S,4S,5R,6R)-6-azido-2,3-epoxy-4,5,7-tris(benzyloxy)-2(E)-hepten-1-ol
• 英文别名: (2R,3S,4S,5R,6R)-6-azide-2,3-epoxy-4,5,7-tribenzyloxy-2(E)-hepten-1-ol；[(2R,3S)-3-[(1S,2R,3R)-3-azido-1,2,4-tris(phenylmethoxy)butyl]oxiran-2-yl]methanol
• CAS: 231619-09-3
• 化学式: C₂₈H₃₁N₃O₅
• 分子量: 489.571
• InChiKey: IVCOFOTXOBAYPT-QXLMEFJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-6-azido-2,3-epoxy-4,5,7-tris(benzyloxy)-2(E)-hepten-1-ol 在 palladium on activated charcoal sodium azide 、 氢气 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 potassium iodide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 119.0h， 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,6S)-6-<((chloromethyl)sulfonyl)oxy>-2,3-epoxy-4,5,7-tris(benzyloxy)-2(E)-hepten-1-ol 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以87%的产率得到(2R,3S,4S,5R,6R)-6-azido-2,3-epoxy-4,5,7-tris(benzyloxy)-2(E)-hepten-1-ol
  参考文献：
  名称：

  Synthesis and inhibition analysis of five-membered homoazasugars from D-arabinofuranose via an SN2 reaction of the chloromethylsulfonate

  摘要：

  DOI：

  10.1016/0040-4039(95)01769-e

文献信息

• Synthesis and inhibition analysis of five-membered homoazasugars from D-arabinofuranose via an SN2 reaction of the chloromethylsulfonate
  作者：Sayoko Hiranuma、Takeshi Shimizu、Tadashi Nakata、Tetsuya Kajimoto、Chi-Huey Wong

  DOI：10.1016/0040-4039(95)01769-e

  日期：1995.11
• 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.