N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol | 679404-77-4

• 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: N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol
• 英文别名: benzyl (2R,3R,4R,5R)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidine-1-carboxylate
• CAS: 679404-77-4
• 化学式: C₁₄H₁₉NO₆
• 分子量: 297.308
• InChiKey: OIBMNXFWGHCZMZ-FDYHWXHSSA-N

物化性质

• 沸点：
  494.3±45.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol 在 palladium on activated charcoal 吡啶 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-benzyl-2,6-di-O-pivaloyl-1,5-dideoxy-1,5-imino-D-mannitol
  参考文献：
  名称：

  Synthesis of an iminosugar based peptidomimetic analogue

  摘要：

  The synthesis of 1-deoxymannojirimycin based analogue of a known HIV-protease inhibitor is described. The strategies employed for introduction of the pharmocophore groups onto the azasugar scafford were based on regioselective reactions of the hydroxly groups of the natural product and of D-fructopyranoside derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.064
• 作为产物：
  描述：

  1-脱氧甘露伊霉素 、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 以74%的产率得到N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol
  参考文献：
  名称：

  Synthesis of an iminosugar based peptidomimetic analogue

  摘要：

  The synthesis of 1-deoxymannojirimycin based analogue of a known HIV-protease inhibitor is described. The strategies employed for introduction of the pharmocophore groups onto the azasugar scafford were based on regioselective reactions of the hydroxly groups of the natural product and of D-fructopyranoside derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.064

文献信息

• Evidence for a Boat Conformation at the Transition State of GH76 α-1,6-Mannanases-Key Enzymes in Bacterial and Fungal Mannoprotein Metabolism
  作者：Andrew J. Thompson、Gaetano Speciale、Javier Iglesias-Fernández、Zalihe Hakki、Tyson Belz、Alan Cartmell、Richard J. Spears、Emily Chandler、Max J. Temple、Judith Stepper、Harry J. Gilbert、Carme Rovira、Spencer J. Williams、Gideon J. Davies

  DOI：10.1002/anie.201410502

  日期：2015.4.27

  QM/MM metadynamics that show how the enzyme surface restricts the conformational landscape of the substrate, rendering the B2,5 conformation the most energetically stable on‐enzyme. We conclude that GH76 enzymes perform catalysis using an itinerary that passes through OS2 and B2,5≠ conformations, information that should inspire the development of new antifungal agents.

  α-甘露糖苷酶和 α-甘露聚糖酶因其在 α-甘露糖苷受阻异头中心的亲核取代以及甘露糖苷酶抑制剂作为细胞探针和治疗剂的潜力而引起了人们的关注。我们报告了通过对米氏复合物的结构分析以及新型氮杂/亚氨基糖抑制剂的合成和评估研究的 GH76 α-甘露聚糖家族的构象路线。O S 2构象的米氏复合物，加上抑制剂复合物中的氮杂糖变形为高能B 2,5构象，通过从头算 QM/MM 元动力学合理化，显示酶表面如何限制酶的构象景观基板，呈现B 2,5构象是能量最稳定的酶。我们得出结论，GH76 酶使用通过O S 2和B 2,5 ≠构象的路线进行催化，这些信息应该会激发新抗真菌剂的开发。
• Synthesis of Somatostatin Mimetics Based on the 1-Deoxymannojirimycin Scaffold
  作者：Sebastien G. Gouin、Paul V. Murphy

  DOI：10.1021/jo051454n

  日期：2005.10.1

  A novel synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin (DMJ) scaffold has been developed. This involved development of a route suitable for the strategic grafting of pharmacophoric tryptophan and lysine side chains to the nitrogen atom of the piperidine ring and to the primary hydroxyl group of DMJ, respectively. The novel peptidomimetics were found to bind with higher affinity

  已开发出一种基于1-deoxymannojirimycin（DMJ）支架的生长抑素模拟物的新型合成方法。这涉及开发适合于将药效团的色氨酸和赖氨酸侧链分别战略性地接枝到哌啶环的氮原子和DMJ的伯羟基的途径。发现新型拟肽与sst4受体的结合比与sst5受体的结合具有更高的亲和力。
• Synthesis of peptidomimetics based on iminosugar and β-d-glucopyranoside scaffolds and inhibiton of HIV-protease
  作者：Florence Chery、Linda Cronin、Julie L O'Brien、Paul V Murphy

  DOI：10.1016/j.tet.2004.05.080

  日期：2004.7

  Synthetic routes to peptidomimetic compounds derived from saccharide scaffolds are described. The regioselective introduction of pivaloyl groups was achieved from N-benzyloxycarbonyl protected 1-deoxymannojirimycin or via D-fructopyranosides. The results from biological evaluation of the saccharide derivatives as HIV-protease inhibitors are included. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of an iminosugar based peptidomimetic analogue
  作者：Florence Chery、Paul V. Murphy

  DOI：10.1016/j.tetlet.2004.01.064

  日期：2004.3

  The synthesis of 1-deoxymannojirimycin based analogue of a known HIV-protease inhibitor is described. The strategies employed for introduction of the pharmocophore groups onto the azasugar scafford were based on regioselective reactions of the hydroxly groups of the natural product and of D-fructopyranoside derivatives. (C) 2004 Elsevier Ltd. All rights reserved.