benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 134308-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,4aR,6R,7R,8R,8aS)-8-hydroxy-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 134308-75-1
• 化学式: C₂₂H₂₅NO₆
• 分子量: 399.444
• InChiKey: NXGXFAKJUWEFEC-CGXUPHRESA-N

物化性质

• 沸点：
  650.6±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 吡啶 、 三乙基硅烷 、 三氟化硼乙醚 、 barium(II) hydroxide 、 barium(II) oxide 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 benzyl 2-acetamido-3-O-propargyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks

  摘要：

  Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.

  DOI：

  10.1021/jo200076z
• 作为产物：
  描述：

  β-D-葡萄糖胺五乙酸酯 在 sodium methylate 、 对甲苯磺酸 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks

  摘要：

  Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.

  DOI：

  10.1021/jo200076z

文献信息

• The use of 2-deoxy-2-trichloroacetamido-d-glucopyranose derivatives in syntheses of oligosaccharides
  作者：Géraldine Blatter、Jean-Marie Beau、Jean-Claude Jacquinet

  DOI：10.1016/0008-6215(94)84038-5

  日期：1994.7

  trichloroacetimidate and its O-benzylated analogue were tested as glycosyl donors in the reaction with a set of sugar acceptors unsubstituted on O-3 and O-4, typically encountered in the synthesis of oligosaccharides. Glycosides were obtained in good to excellent yields with only a slight excess (1.1-1.2 equiv) of the donor, and with a high degree of 1,2-trans stereoselectivity. The corresponding 2-(trich

  测试了3,4,6-三-O-乙酰基-2-脱氧-2-三氯乙酰氨基-α-D-吡喃葡糖基三氯乙酰亚氨酸酯及其O-苄基类似物与一组未在O上取代的糖受体在反应中的糖基供体-3和O-4，通常在寡糖合成中遇到。以良好至极好的收率获得糖苷，仅略微过量（1.1-1.2当量）的供体，并具有高度的1，2-反式立体选择性。假定相应的2-（三氯甲基）恶唑啉鎓离子是主要的反应性中间体。在中性条件下，通过用三丁基锡烷还原，二糖产物中的N-三氯乙酰基很容易转化为N-乙酰基。
• Monosaccharide inhibitors targeting carbohydrate esterase family 4 de-N-acetylases
  作者：Benjamin R. DiFrancesco、Zachary A. Morrison、Mark Nitz

  DOI：10.1016/j.bmc.2018.10.008

  日期：2018.11

  Carbohydrate Esterase family 4 contains virulence factors which modify peptidoglycan and biofilm-related exopolysaccharides. Despite the importance of this family of enzymes, a potent mechanism-based inhibition strategy has yet to emerge. Based on the postulated tridentate binding mode of the tetrahedral de-N-acetylation intermediate, GlcNAc derivatives bearing metal chelating groups at the 2 and 3 positions

  碳水化合物酯酶家族4包含可改变肽聚糖和生物膜相关胞外多糖的毒力因子。尽管该酶家族很重要，但基于机理的有效抑制策略尚未出现。基于假定的四面体脱-N-乙酰化中间体的三齿结合模式，合成了在2和3位带有金属螯合基团的GlcNAc衍生物。这些支架包括2-C膦酸酯，2-C磺酰胺，2-硫代乙酰胺弹头以及在3-位带有巯基，胺和叠氮化物取代基的衍生物。对这些抑制剂针对代表性的肽聚糖脱乙酰酶（来自肺炎链球菌肺炎的Pgda）进行了测定，和代表性的生物膜相关胞外多糖脱乙酰基酶，PgaB从大肠杆菌。在评估的抑制剂中，3-硫代衍生物对Pgda的抑制作用弱到中等。最强的抑制剂是2,3-二甲氧基苄基-2-硫代乙酰胺-3-硫代-β- d-葡萄糖苷，其抑制能力显示出对金属浓度的出乎意料的依赖性，并且发现其具有部分混合抑制模式（K i  = 2.9 ±0.6μM）。
• Synthesis of 2-Amino glycal Derivatives and their Conversion into Highly Functionalised β-Enamino Ketones
  作者：Fernando Iglesias-Guerra、Ignacio Periñán、Margarita Vega-Holm、José M. Vega-Pérez

  DOI：10.1002/ejoc.201000325

  日期：2010.8

  A general method for the synthesis of 2-amino glycals employing 2-amino sugar derivatives as precursors is described. A new 2-(amino-disubstituted) glycal backbone is obtained independently of the aglycon and nitrogen substituents, the configuration of the C-1, C-2 and C-3 atoms of the starting amino sugar and the oxidative system employed. The reactivity of these new 2-amino glycals with amines has

  描述了使用 2-氨基糖衍生物作为前体合成 2-氨基糖的通用方法。新的 2-（氨基二取代）糖基主链的获得与苷元和氮取代基、起始氨基糖的 C-1、C-2 和 C-3 原子的构型以及所采用的氧化系统无关。已经研究了这些新的 2-氨基聚糖与胺的反应性。反应是用两种不同的 N-取代氨基糖醛和各种烷基胺和芳基胺进行的。通过该方法获得高度官能化的β-烯氨基酮。
• Oxazolidines from sugars: conformationally restricted derivatives of muramic acid
  作者：José M. Vega-Pérez、José L. Espartero、Francisco J. Ruiz、Felipe Alcudia

  DOI：10.1016/0008-6215(92)80057-8

  日期：1992.8

  Abstract The syntheses are described of four conformationally restricted derivatives of muramic acid based on the α- d -glucopyrano[2,3- d ]oxazolidine ring system.

  摘要描述了基于α-d-吡喃并吡喃并[2,3-d]恶唑烷环系统的四种构象受限的山梨酸衍生物的合成。
• Synthesis of 1,2-cis- and 1,2-trans-glycosides of 2-acetamido-4,6-O-benzylidene-2-deoxy-d-glucopyranose by anomeric O-alkylation
  作者：Sergey S. Pertel、Oksana A. Gorkunenko、Elena S. Kakayan、Vasily Ja. Chirva

  DOI：10.1016/j.carres.2011.01.016

  日期：2011.4

  The reaction of a partially protected 1-hydroxy derivative of N-acetyl-D-glucosamine with benzyl bromide under conditions of anomeric O-alkylation was studied. It was found that the stereoselectivity of the reaction depended on the nature of the alkali metal cation constituent of a transient ion pair. The substitution of the Li(+) cation for K(+) or complexation with a crown ether allowed the steric

  研究了在异头O-烷基化条件下N-乙酰基-D-葡糖胺的部分保护的1-羟基衍生物与苄基溴的反应。发现反应的立体选择性取决于瞬态离子对的碱金属阳离子成分的性质。Li（+）阳离子取代K（+）或与冠醚络合使得空间结果从β-选择性转变为α-选择性。