1,3,4,6-tetra-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranose | 56644-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranose
• 英文别名: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranoside；[(2R,3S,4R,5R,6R)-3,4,6-triacetyloxy-5-[(2,2,2-trichloroacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 56644-75-8
• 化学式: C₁₆H₂₀Cl₃NO₁₀
• 分子量: 492.695
• InChiKey: SEEYXQVYXYGHNF-KSTCHIGDSA-N

物化性质

• 沸点：
  551.9±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-amino-2-deoxy-1,3,4,6-tetra-O-(trimethylsilyl)-α-D-glucopyranose 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranose
  参考文献：
  名称：

  -O-三甲基甲硅烷基化糖的非端基的选择性乙酰化

  摘要：

  糖的羟基的选择性修饰由于其近乎相对的反应性而一直是一个长期的挑战。本文中，我们报道了TMSOTf催化的几种过O -TMS保护的糖底物的非异头羟基的选择性乙酰化，同时不影响其异头基团。除了本身具有通用性之外，可以将完整的异头O -TMS基团官能化，以提供关键的糖前体，如亚氨酸酯供体，否则可以通过逐步的异头脱保护-官能化程序进行合成。

  DOI：

  10.1021/acs.joc.0c02813

文献信息

• Synthesis and Scalable Conversion of <scp>l</scp>-Iduronamides to Heparin-Related Di- and Tetrasaccharides
  作者：Steen U. Hansen、Gavin J. Miller、Marek Baráth、Karl R. Broberg、Egle Avizienyte、Madeleine Helliwell、James Raftery、Gordon C. Jayson、John M. Gardiner

  DOI：10.1021/jo300722y

  日期：2012.9.21

  structure is also reported for the novel, 4C1-conformationally locked bicyclic 1,6-anhydro iduronate lactone along with an X-ray structures of a novel distorted 4C1 iduronate 4,6-lactone. Deuterium labeling also provides mechanistic insight into the formation of lactone products during the novel amyl nitrite-mediated hydrolysis of iduronamide into the parent iduronic acid functionality.

  可按千克规模制备的非对映异构纯氰醇可在一个步骤中有效转化为新型l-艾杜隆酰胺。这种艾杜糖醛酰胺的新区域选择性酰化和亚硝酸戊酯介导的新型温和酰胺水解方法能够实现短时间、可扩展的l-艾杜糖醛酸二乙酸酯 C-4 受体的合成，以及l-艾杜糖醛酸 C-4 受体硫糖苷。描述了将这些有效转化为一系列肝素相关葡萄糖-碘二糖构建块（各种 C-4 保护选项），包括对关键肝素构建块 ido-硫糖苷供体的高效多克访问。1-OAc 二糖通过分化为受体和供体二糖而转化为肝素相关四糖。1,2-二乙酰艾杜糖醛酸甲酯和类似艾杜糖酰胺的X射线和核磁共振数据表明，虽然两者在溶液中均采用1 C 4构象，但艾杜糖醛酸酯在固态时采用4 C 1构象。还报道了新型4 C 1的 X 射线结构-构象锁定双环 1,6-脱水艾糖醛酸内酯以及新型扭曲的4 C 1艾糖醛酸内酯4,6-内酯的 X 射线结构。氘标记还提供了在新型亚硝酸戊酯介导的艾杜糖醛
• 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。
• Modular automated solid phase synthesis of dermatan sulfate oligosaccharides
  作者：Jeyakumar Kandasamy、Frank Schuhmacher、Heung Sik Hahm、James C. Klein、Peter H. Seeberger

  DOI：10.1039/c3cc48860h

  日期：——

  extracellular matrix. Orthogonally protected D-galactosamine and L-iduronic acid building blocks and a photo-cleavable linker are instrumental for the automated synthesis of dermatan sulfate oligosaccharides. Conjugation-ready oligosaccharides were obtained in good yield.

  硫酸皮肤素是糖胺聚糖多糖，其作为细胞外基质的一部分具有多种生物学作用。正交保护的D-半乳糖胺和L-艾杜糖醛酸结构单元以及可光裂解的接头对于硫酸皮肤素寡糖的自动合成至关重要。以高收率获得了易于结合的寡糖。
• Glycoconjugates and use thereof as vaccine against Shigella flexneri serotype 3a and X
  申请人：Mulard Laurence

  公开号：US08815239B2

  公开（公告）日：2014-08-26

  The present invention relates to compounds derived from sugars which reproduce the epitopes of Shigella flexneri serotypes 3a and X and to the use thereof for the preparation of vaccine compositions. More specifically, the subject matter of the present invention relates to novel glycoconjugated compounds comprising oligosaccharides or polysaccharides described hereinafter, to the method for synthesizing these oligosaccharides or polysaccharides and glycoconjugates, to derivatives of these oligosaccharides or polysaccharides, to compositions containing same, and also to the use of the glycoconjugates for vaccination purposes. Finally, the present invention relates to methods for diagnosing a Shigella flexneri infection using one or more oligosaccharides or polysaccharides or conjugates thereof.

  本发明涉及从糖类衍生的化合物，其重现志贺氏菌弗氏菌血清型3a和X的表位，并且涉及将其用于制备疫苗组合物。更具体地，本发明涉及包括下文描述的寡糖或多糖的新型糖结合化合物，用于合成这些寡糖或多糖和糖结合物的方法，这些寡糖或多糖的衍生物，含有这些衍生物的组合物，以及将糖结合物用于疫苗目的的用途。最后，本发明涉及使用一个或多个寡糖或多糖或其结合物诊断志贺氏菌弗氏菌感染的方法。
• CARBOHYDRATE BASED TOLL-LIKE RECEPTOR (TLR) ANTAGONISTS
  申请人：Upadhyay Shakti

  公开号：US20090215710A1

  公开（公告）日：2009-08-27

  The invention provides carbohydrate based compounds, methods of preparation, and compositions useful for modulating signaling through Toll-like receptors. The methods involve contacting a TLR-expressing cell with a carbohydrate based compound of the invention having a core structure comprising of one or more sugar moieties. The carbohydrate based compounds are useful for inhibiting immune stimulation involving TLR ligands, especially TLR4 and TLR2. The compounds also are suitable for inhibition of inflammatory conditions resulting from infections. The compounds have use in the treatment of inflammation, autoimmunity, allergy, asthma, graft rejection, graft versus host disease, infection, sepsis, cancer, and immunodeficiency.

  该发明提供了基于碳水化合物的化合物、制备方法和组合物，用于调节通过Toll样受体的信号传导。该方法涉及将表达TLR的细胞与该发明的基于碳水化合物接触，其核心结构包括一个或多个糖基团。基于碳水化合物的化合物可用于抑制涉及TLR配体的免疫刺激，特别是TLR4和TLR2。这些化合物还适用于抑制由感染引起的炎症症状。这些化合物在治疗炎症、自身免疫、过敏、哮喘、移植排斥、移植物抗宿主病、感染、败血症、癌症和免疫缺陷方面有用。