2-chloroethyl 2-acetamido-2-deoxy-α-D-glucopyranoside | 2495-94-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloroethyl 2-acetamido-2-deoxy-α-D-glucopyranoside
• 英文别名: 2-Chloroethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside；N-[(2S,3R,4R,5S,6R)-2-(2-chloroethoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 2495-94-5
• 化学式: C₁₀H₁₈ClNO₆
• 分子量: 283.709
• InChiKey: LXIKSHBBSCNHHT-IGORNWKESA-N

物化性质

• 沸点：
  579.1±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-chloroethyl 2-acetamido-2-deoxy-α-D-glucopyranoside 在 吡啶 、 sodium azide 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 69.0h， 生成 2-azidoethyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Cu(II)-Self-assembling bipyridyl-glycoclusters and dendrimers bearing the Tn-antigen cancer marker: syntheses and lectin binding properties

  摘要：

  Using the carbohydrate cancer marker, T-N-antigen (alpha-GalNAc-OR), covalently linked to a bipyridine core, square planar complexes were formed by self-assembly upon simple addition of Cu(11) sulfate. The required alpha-D-GalNAc-OR building block was constructed from 2-azidoethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside (GlcNAc) by epimerization at C-4 of a suitably protected derivative followed by conventional modifications to provide 2-aminoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-galactopyranoside. The 2-aminoethyl aglycone was further elongated into a key monomer having an aminocaproic acid spacer together with their corresponding dimers using a double N-alkylation strategy of their N-bromoacetyl derivatives using mono-Boc-1,4-diaminobutane, respectively. The building blocks containing the bipyridyl dimers, having either a short or a long spacer arm, together with the tetramer built from the short spacer derivative were prepared in a convergent manner using 2,2'-bipyridine-4,4'-dicarboxylic acid chloride and the aminated sugar derivatives, respectively. Copper(II)-nucleated GalNAc derivatives containing four and eight residues were obtained from an aqueous solution of the bipyridyl derivatives. The relative inhibitory potencies of these glycodendrimers were evaluated against monomeric allyl alpha-D-GalNAc using a solid-phase competition assay with asialoglycophorin and horseradish peroxidase-labeled lectin Vicia villosa. The di- and tetra-valent bipyridyl clusters showed up to 87-fold increased inhibitory properties (IC50 7.14, 1.82, 4.09 muM, respectively) when compared to the monomer (IC50 158.3 muM) while the Cu(II)-complexes showed up to a 259-fold increase potencies (IC50 0.61 muM) with the octamer showing the highest affinity. However, when expressed on a per-saccharide basis, the tetramer Cu(II) nucleated derivative, possessing the longest inter-sugar distances showed the highest affinity (IC50 0.63 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00438-1
• 作为产物：
  描述：

  D-GlcNAc 、 2-氯乙醇 在 三氟化硼乙醚 作用下， 反应 4.0h， 以63%的产率得到2-chloroethyl 2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  碳水化合物基大内酯的合成及其作为离子识别和催化受体的应用

  摘要：

  聚糖大内酯表现出许多有趣的生物学特性，它们在分子识别和超分子化学中也很重要。因此，能够获得具有不同尺寸和功能的糖大环非常重要。设计并合成了一系列新的含有三唑和内酯部分的基于碳水化合物的大环化合物。该合成以大环化步骤的分子内亲核取代反应为特征。在本文中，评估了一些常见磺酸盐离去基团对大内酯化的影响。使用甲苯磺酸酯对单内酯化产物具有良好的选择性和良好的产率。已经合成并表征了14个不同的大环，其中11个大环来自N-乙酰基D-葡糖胺衍生物的C1至C6位置的环化，另外3个大环来自官能化的D-葡糖胺衍生物的C2至C6环化。这些新型大环内酯具有独特的结构，并表现出有趣的阴离子结合特性，特别是对于氯离子。含有两个三唑的大环与硫酸铜形成配合物，它们是硫酸铜介导的叠氮-炔环加成反应（CuAAC）的有效配体。此外，一些大环化合物对不同的炔烃表现出一定的选择性。

  DOI：

  10.3390/molecules26113394

文献信息

• Modulating Heparanase Activity: Tuning Sulfation Pattern and Glycosidic Linkage of Oligosaccharides
  作者：Sanyong Zhu、Jiayi Li、Ravi S. Loka、Zhenfeng Song、Israel Vlodavsky、Kezhong Zhang、Hien M. Nguyen

  DOI：10.1021/acs.jmedchem.0c00156

  日期：2020.4.23

  Heparanase cleaves polymeric heparan sulfate (HS) molecules into smaller oligosaccharides, allowing for release of angiogenic growth factors promoting tumor development and autoreactive immune cells to reach the insulin-producing β cells. Interaction of heparanase with HS chains is regulated by specific substrate sulfation sequences. We have synthesized 11 trisaccharides that are highly tunable in

  乙酰肝素酶将聚合的硫酸乙酰肝素（HS）分子裂解为较小的寡糖，从而释放促血管生成生长因子，从而促进肿瘤的发展，并使自身反应性免疫细胞到达产生胰岛素的β细胞。乙酰肝素酶与HS链的相互作用受特定底物硫酸化序列的调节。我们已经合成了11种在结构和硫酸化模式上高度可调的三糖，使我们能够确定乙酰肝素酶如何识别HS底物并选择有利的切割位点。我们的研究表明（1）三糖的+1位亚基上的N-SO3-和-2位亚基上的6-O-SO3-对乙酰肝素酶识别至关重要，（2）在-1位亚基上添加2-O-SO3- 3-O-SO3-转化为GlcN单元是不利的，（3）还原端的异头构型（α或β）对于控制乙酰肝素酶活性至关重要。我们的研究还表明，在-2和+1亚位处具有N-和6-O-SO3-的α-三糖抑制了乙酰肝素酶并具有抗水解性。
• Syntheses of <i>Bis</i> ‐Triazole Linked Carbohydrate Based Macrocycles and Their Applications for Accelerating Copper Sulfate Mediated Click Reaction
  作者：Anji Chen、Lalith P. Samankumara、Sanjeeva Dodlapati、Dan Wang、Surya Adhikari、Guijun Wang

  DOI：10.1002/ejoc.201801714

  日期：2019.2.14

  Eight glucosamine based 1,2,3‐triazole linked macrocycles were synthesized starting from the readily available N‐acetyl‐d‐glucosamine. These bis‐triazole‐linked glycomacrocycles showed remarkable rate acceleration for CuSO4 mediated azide and alkyne cycloaddition reactions in aqueous solutions.

  八个葡糖胺基于1,2,3-三唑连接的大环化合物合成从容易获得的起始N-乙酰基- d -葡糖胺。这些双三唑连接的糖大环化合物在水溶液中对CuSO 4介导的叠氮化物和炔烃环加成反应显示出显着的速率加速。
• Heparan sulfate glycomimetics <i>via</i> iterative assembly of “clickable” disaccharides
  作者：Cangjie Yang、Yu Deng、Yang Wang、Chaoshuang Xia、Akul Y. Mehta、Kelly J. Baker、Anuj Samal、Putthipong Booneimsri、Chanthakarn Lertmaneedang、Seung Hwang、James P. Flynn、Muqing Cao、Chao Liu、Alec C. Zhu、Richard D. Cummings、Cheng Lin、Udayan Mohanty、Jia Niu

  DOI：10.1039/d3sc00260h

  日期：——

  Iterative assembly of variably sulfated clickable disaccharides facilely produced mass spec-sequencible heparan sulfate mimetics. These glycomimetic oligomers bind protein in a sulfation-dependent manner consistent with that of the native glycans.

  通过迭代组装硫酸化程度不同的可点击二糖，可方便地制备出质谱序列可追溯的硫酸肝素模拟物。这些拟糖寡聚体以硫酸化依赖性方式结合蛋白质，与原生聚糖的结合方式一致。
• Synthetic assembly of α-O-linked-type GlcNAc using polymer chemistry affords sugar clusters, which effectively bind to lectins
  作者：Jyuichi Nakada、Takahiko Matsushita、Tetsuo Koyama、Ken Hatano、Koji Matsuoka

  DOI：10.1016/j.bmcl.2024.129616

  日期：2024.2
• Synthesis of Carbohydrate Based Macrolactones and Their Applications as Receptors for Ion Recognition and Catalysis
  作者：Surya B. Adhikari、Anji Chen、Guijun Wang

  DOI：10.3390/molecules26113394

  日期：——

  cyclization of functionalized D-glucosamine derivatives. These novel macrolactones have unique structures and demonstrate interesting anion binding properties, especially for chloride. The macrocycles containing two triazoles form complexes with copper sulfate, and they are effective ligands for copper sulfate mediated azide-alkyne cycloaddition reactions (CuAAC). In addition, several macrocycles show

  聚糖大内酯表现出许多有趣的生物学特性，它们在分子识别和超分子化学中也很重要。因此，能够获得具有不同尺寸和功能的糖大环非常重要。设计并合成了一系列新的含有三唑和内酯部分的基于碳水化合物的大环化合物。该合成以大环化步骤的分子内亲核取代反应为特征。在本文中，评估了一些常见磺酸盐离去基团对大内酯化的影响。使用甲苯磺酸酯对单内酯化产物具有良好的选择性和良好的产率。已经合成并表征了14个不同的大环，其中11个大环来自N-乙酰基D-葡糖胺衍生物的C1至C6位置的环化，另外3个大环来自官能化的D-葡糖胺衍生物的C2至C6环化。这些新型大环内酯具有独特的结构，并表现出有趣的阴离子结合特性，特别是对于氯离子。含有两个三唑的大环与硫酸铜形成配合物，它们是硫酸铜介导的叠氮-炔环加成反应（CuAAC）的有效配体。此外，一些大环化合物对不同的炔烃表现出一定的选择性。