2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide | 76670-94-5

• 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: 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide
• 英文别名: 2,3,4,6-Tetra-O-benzyl-D-xylo-hex-5-ulosonamide；(2R,3S,4S)-5-oxo-2,3,4,6-tetrakis(phenylmethoxy)hexanamide
• CAS: 76670-94-5
• 化学式: C₃₄H₃₅NO₆
• 分子量: 553.655
• InChiKey: BEQCQVWVGURTRP-XKKJXBDVSA-N

物化性质

• 沸点：
  740.7±60.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide 在 lithium aluminium tetrahydride 、 甲酸 、 三氯化硼 、 sodium cyanoborohydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 30.0h， 生成 米格鲁他
  参考文献：
  名称：

  Total synthesis of N-butyl-1-deoxynojirimycin

  摘要：

  N-Butyl-1-deoxynojirimycin (NB-DNJ) derived from imino sugar deoxynojirimycin (DNJ) has been approved for the treatment of Gaucher's disease. Herein, a facile and efficient synthetic procedure for NB-DNJ has been described. Comparing to the methods reported previously, methanesulfonyl group was used as a leaving group for easy displacement upon attack by the imine in the sugar ring, leading to a high yield during the introduction of the n-butyl group. This method can serve as an excellent protocol for the synthesis of DNJ derivatives with a variety of N-alkyl substituents and for large-scale production.

  DOI：

  10.1080/07328303.2017.1330415
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 氨 、 乙酸酐 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide
  参考文献：
  名称：

  Structure–activity relationships in a series of C2-substituted gluco-configured tetrahydroimidazopyridines as β-glucosidase inhibitors

  摘要：

  Inhibition of glycoside hydrolases has widespread application in treatment of diabetes, viral infections, lysosomal storage diseases and cancers. Gluco-configured tetrahydroimidazopyridines are the most potent beta-glucosidase inhibitors reported to date. Using transition state mimic strategy, a series of C2-substituted gluco-configured tetrahydroimidazopyridines were designed and synthesized. Compounds 3 (K-i = 0.64 nM) and 5 (K-i = 0.58 nM) showed stronger inhibitory potency against beta-glucosidase. Maestro 9.1 was used to study the structure-activity relationships by docking the compounds into the beta-glucosidase active sites. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.043

文献信息

• Synthesis of 1-Deoxynojirimycin: Exploration of Optimised Conditions for Reductive Amidation and Separation of Epimers
  作者：Mehwish Iftikhar、Lin Wang、Zhijie Fang

  DOI：10.3184/174751917x15000341607489

  日期：2017.8

  1-Deoxynojirimycin (DNJ), which has importance with respect to sugar processing enzymes, is a synthetic target for chemists. A key step in the synthesis of DNJ is the preparation of 2,3,4,6-tetra-O-benzyl-D-glucono-δ-lactam. By varying reaction parameters such as temperature, solvent and reducing reagent, improvements on previous methods are described. A novel approach for the synthesis of 2,3,4,6

  1-脱氧野尻霉素 (DNJ) 对糖加工酶具有重要意义，是化学家的合成目标。DNJ 合成的关键步骤是制备 2,3,4,6-四-O-苄基-D-葡萄糖酸-δ-内酰胺。通过改变温度、溶剂和还原剂等反应参数，描述了对先前方法的改进。使用 PCC 作为氧化剂开发了一种合成 2,3,4,6-tetra-O-benzyl-5-dehydro-5-deoxo-D-gluconamide 的新方法。差向异构体的分离允许在还原和氢解步骤后以 85% 的产率获得 DNJ。
• 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。
• Glycosidase Inhibition with Fullerene Iminosugar Balls: A Dramatic Multivalent Effect
  作者：Philippe Compain、Camille Decroocq、Julien Iehl、Michel Holler、Damien Hazelard、Teresa Mena Barragán、Carmen Ortiz Mellet、Jean-François Nierengarten

  DOI：10.1002/anie.201002802

  日期：——

  Superball! A dodecavalent iminosugar derivative with a fullerene core (see picture) shows a binding enhancement of up to three orders of magnitude over the corresponding monovalent ligand in glycosidase inhibition assays. This is the first evidence of a significant multivalent effect in glycosidase inhibition.

  超级球！在糖苷酶抑制试验中，具有富勒烯核心的十二价亚氨基糖衍生物（参见图片）显示出比相应的单价配体高多达三个数量级的结合增强作用。这是糖苷酶抑制作用显着的多价作用的第一个证据。
• A facile transformation of sugar lactones to azasugars
  作者：Herman S. Overkleeft、Jim van Wiltenburg、Upendra K. Pandit

  DOI：10.1016/s0040-4020(01)86715-6

  日期：1994.4

  The synthesis of pyrano- and furano- sugar lactams from the corresponding lactones, in a five step sequence, is described.
• An expedient stereoselective synthesis of gluconolactam
  作者：Herman S. Overkleeft、Jim van Wiltenburg、Pandit K. Upendra

  DOI：10.1016/s0040-4039(00)60459-8

  日期：1993.4

  An efficient synthesis of the title compound, starting from glucose, is described.