(3S,4R,5S,6S)-3-benzylamino-4,5,7-tribenzyloxy-6-hydroxyhept-1-ene | 872360-63-9

• 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: (3S,4R,5S,6S)-3-benzylamino-4,5,7-tribenzyloxy-6-hydroxyhept-1-ene
• 英文别名: (2S,3R,4R,5S)-5-(benzylamino)-1,3,4-tris(phenylmethoxy)hept-6-en-2-ol
• CAS: 872360-63-9
• 化学式: C₃₅H₃₉NO₄
• 分子量: 537.699
• InChiKey: NEAQNLWNNHHMPI-NUXXNWGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,6S)-3-benzylamino-4,5,7-tribenzyloxy-6-hydroxyhept-1-ene 在 吡啶 、 sodium tetrahydroborate 、 硫酸 、 臭氧 、 甲基磺酰氯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.42h， 生成 (2S,3R,4R,5R)-N-benzyl-3,4-dibenzyloxy-5-[(benzyloxy)methyl]-2-hydroxymethyl-pyrrolidine
  参考文献：
  名称：

  Iminosugars as glycosyltransferase inhibitors: synthesis of polyhydroxypyrrolidines and their evaluation on chitin synthase activity

  摘要：

  Chitin synthase is an enzyme involved in the biosynthesis of chitin, a major structural component of the cell wall of many fungi. Since chitin is absent in vertebrates, chitin synthase has been envisaged as a valuable target in the search for new antifungal agents. In this report, a series of C-2 substituted polyhydroxypyrrolidines were designed and synthesized with the aim of mimicking the glycosylcation involved at the transition state of the enzymatic reaction governed by chitin synthase. Some of these models displayed chitin synthase inhibition in the millimolar range. However, no significant antifungal activity was noted on a panel of fungal strains. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.001
• 作为产物：
  描述：

  乙烯基溴化镁 、 N-benzyl-2,3,5-tri-O-benzyl-L-xylofuranosylamine 以 四氢呋喃 为溶剂， 反应 7.0h， 以91%的产率得到(3S,4R,5S,6S)-3-benzylamino-4,5,7-tribenzyloxy-6-hydroxyhept-1-ene
  参考文献：
  名称：

  Iminosugars as glycosyltransferase inhibitors: synthesis of polyhydroxypyrrolidines and their evaluation on chitin synthase activity

  摘要：

  Chitin synthase is an enzyme involved in the biosynthesis of chitin, a major structural component of the cell wall of many fungi. Since chitin is absent in vertebrates, chitin synthase has been envisaged as a valuable target in the search for new antifungal agents. In this report, a series of C-2 substituted polyhydroxypyrrolidines were designed and synthesized with the aim of mimicking the glycosylcation involved at the transition state of the enzymatic reaction governed by chitin synthase. Some of these models displayed chitin synthase inhibition in the millimolar range. However, no significant antifungal activity was noted on a panel of fungal strains. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.001

文献信息

• Iminosugars as glycosyltransferase inhibitors: synthesis of polyhydroxypyrrolidines and their evaluation on chitin synthase activity
  作者：Isabelle Gautier-Lefebvre、Jean-Bernard Behr、Georges Guillerm、Murielle Muzard

  DOI：10.1016/j.ejmech.2005.07.001

  日期：2005.12

  Chitin synthase is an enzyme involved in the biosynthesis of chitin, a major structural component of the cell wall of many fungi. Since chitin is absent in vertebrates, chitin synthase has been envisaged as a valuable target in the search for new antifungal agents. In this report, a series of C-2 substituted polyhydroxypyrrolidines were designed and synthesized with the aim of mimicking the glycosylcation involved at the transition state of the enzymatic reaction governed by chitin synthase. Some of these models displayed chitin synthase inhibition in the millimolar range. However, no significant antifungal activity was noted on a panel of fungal strains. (c) 2005 Elsevier SAS. All rights reserved.