(2R,3S,4R,5R)-N-benzyl-5-hydroxy-2,3,4,6-tetrabenzyloxyhexanamide | 128984-82-7

• 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,4R,5R)-N-benzyl-5-hydroxy-2,3,4,6-tetrabenzyloxyhexanamide
• 英文别名: N-Benzyl-2,3,4,6-tetra-O-benzyl-D-gluconamide；(2R,3S,4R,5R)-N-benzyl-5-hydroxy-2,3,4,6-tetrakis(phenylmethoxy)hexanamide
• CAS: 128984-82-7
• 化学式: C₄₁H₄₃NO₆
• 分子量: 645.796
• InChiKey: WEFOEJREDHDXOW-OPGJLUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R)-N-benzyl-5-hydroxy-2,3,4,6-tetrabenzyloxyhexanamide 在 Amberlite IR 120 H+ 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以88%的产率得到5-内酯
  参考文献：
  名称：

  对所谓的“轻柔合成诺奇霉素的评论”

  摘要：

  DOI：

  10.1016/s0040-4039(00)94567-2
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 二甲基亚砜 作用下， 以 乙酸酐 、 甲苯 为溶剂， 反应 20.0h， 生成 (2R,3S,4R,5R)-N-benzyl-5-hydroxy-2,3,4,6-tetrabenzyloxyhexanamide
  参考文献：
  名称：

  Synthesis of protected sugar-amino acid hybrid molecules as platform for further derivatization

  摘要：

  The sugar-amino acid hybrid molecules with appropriate protecting groups were synthesized from sugar-derived lactones and ester of amino acids in five high yielding steps. The C-5 of the resultant hybrid molecule, upon selective deprotection, can be further derivatized to afford the linear depsipeptide. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.042

文献信息

• Metal-Free One-Pot Oxidative Amidation of Aldoses with Functionalized Amines
  作者：Ludovic Colombeau、Ténin Traoré、Philippe Compain、Olivier R. Martin

  DOI：10.1021/jo801626v

  日期：2008.11.7

  Metal-free one-pot oxidative amidation of aldoses with functionalized amines using iodine provides a rapid access to functionalized aldonamides. The main advantage of this approach relies on the fact that aldehyde oxidation and C-N bond formation are performed in a single synthetic operation.

  使用碘将醛糖与功能化胺进行无金属一锅氧化酰胺化反应，可快速获得功能化醛酰胺。该方法的主要优点依赖于这样的事实，即醛的氧化和CN键的形成是在单个合成操作中进行的。
• Synthesis of glycosylamines and glyconamides using molecular iodine
  作者：Maxime B. Fusaro、Vincent Chagnault、Denis Postel

  DOI：10.1016/j.tet.2012.11.027

  日期：2013.1

  We describe herein the synthesis of glyconamides and glycosylamines using molecular iodine on benzylated carbohydrates. During the improvement and the optimization of the direct oxidative amidation reaction, we also discovered the possibility to form glycosylamines with excellent yields and short reaction times in comparison with the previously reported procedures. Advantages of these methods are the

  我们在本文中描述了在苄基化碳水化合物上使用分子碘合成糖苷和糖胺。在直接氧化酰胺化反应的改进和优化过程中，我们还发现与以前报道的方法相比，可以以极高的收率和较短的反应时间形成糖胺。这些方法的优点是操作简单，无需使用复杂的试剂和程序，以及反应的一般性。我们的方法是获得N-烷基亚氨基糖和亚氨基C-糖苷前体的绝佳途径。
• Cyclization Dichotomy of D-xylo-Hex-5-ulosonamides and Synthesis of Piperidine Analogs of Aldohexoses and Aldohexono-1,5-lactones
  作者：Radka Kováříková、Miroslav Ledvina、David Šaman

  DOI：10.1135/cccc19990673

  日期：——

  The preparation of 2,3,4,6-tetra-O-benzyl-5-D-xylo-hex-5-ulosonamides 3a and 3b and their cyclization to 5-amino-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucono-1,5-lactam (4) and 5-amino- 2,3,4,6-tetra-O-benzyl-5-deoxy-D-talono-1,5-lactam (5) or to 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol (9), and also their direct transformation into 2,3,4,6-tetra-O-benzyl- D-talono-1,5-lactone (6), are described and discussed. The atypical boat conformation of D-talonolactam 5 and D-talonolactone 6 was found.

  2,3,4,6-四O-苄基-5-D-木糖-己-5-乌洛磺酰胺3a和3b的制备以及它们环化为5-氨基-2,3,4,6-四O-苄基-5-脱氧-D-葡萄糖酮-1,5-内酯(4)和5-氨基-2,3,4,6-四O-苄基-5-脱氧-D-他糖酮-1,5-内酯(5)或2,3,4,6-四O-苄基-1,5-二脱氧-1,5-亚胺-D-葡萄糖醇(9)，以及它们直接转化为2,3,4,6-四O-苄基-D-他糖-1,5-内酯(6)，被描述和讨论。发现了D-他糖内酯5和D-他糖内酯酮6的非典型舟型构象。
• FLEET, GEORGE W. J.;RAMSDEN, NIGEL G.;CARPENTER, NEIL M.;PETURSSON, SIGTH+, TETRAHEDRON LETT., 31,(1990) N, C. 405-408
  作者：FLEET, GEORGE W. J.、RAMSDEN, NIGEL G.、CARPENTER, NEIL M.、PETURSSON, SIGTH+

  DOI：——

  日期：——
• Synthesis of protected sugar-amino acid hybrid molecules as platform for further derivatization
  作者：Han Liu、Xuechen Li

  DOI：10.1016/j.tetlet.2012.10.042

  日期：2012.12

  The sugar-amino acid hybrid molecules with appropriate protecting groups were synthesized from sugar-derived lactones and ester of amino acids in five high yielding steps. The C-5 of the resultant hybrid molecule, upon selective deprotection, can be further derivatized to afford the linear depsipeptide. (C) 2012 Elsevier Ltd. All rights reserved.