N-acetyl-α-D-neuraminosyl-(2->6)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)-[N-acetyl-α-D-neuraminosyl-(2->6)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl(1->6)]-β-D-mannopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranose | 724750-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetyl-α-D-neuraminosyl-(2->6)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)-[N-acetyl-α-D-neuraminosyl-(2->6)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl(1->6)]-β-D-mannopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranose
• 英文别名: NeuAc(a2-6)Gal(b1-4)GlcNAc(b1-2)Man(a1-3)[NeuAc(a2-6)Gal(b1-4)GlcNAc(b1-2)Man(a1-6)]Man(b1-4)GlcNAc；(2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2S,3S,4S,5S,6R)-2-[[(2R,3R,4S,5S,6S)-4-[(2R,3S,4S,5S,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4S,5R,6R)-6-[[(2R,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 724750-51-0
• 化学式: C₇₆H₁₂₅N₅O₅₇
• 分子量: 2020.83
• InChiKey: VFNZVHISCAMHMJ-ZAWSQWKFSA-N

物化性质

• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -22
• 重原子数：
  138
• 可旋转键数：
  39
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  982
• 氢给体数：
  36
• 氢受体数：
  57

反应信息

• 作为反应物：
  描述：

  N-acetyl-α-D-neuraminosyl-(2->6)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)-[N-acetyl-α-D-neuraminosyl-(2->6)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl(1->6)]-β-D-mannopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranose 在 2-azido-1,3-dimethylimidazolinium hexafluorophosphate 、 三乙胺 作用下， 以 重水 、 乙腈 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  直接从还原糖中免保护的无糖一锅合成方法

  摘要：

  糖类转化为拟糖模拟物通常涉及多个保护基团操纵。迫切需要开发一种方法，以将高糖和立体选择性过程中的游离糖直接水转化为糖苷，并模拟寡糖和糖缀合物。六氟磷酸2-叠氮基-1,3-二甲基咪唑啉鎓与Cu催化的Huisgen环加成反应的结合使用，可以直接在含水条件下通过还原糖在一步反应中合成一系列糖结合物。该反应是完全立体选择性的，可用于三唑连接的糖苷，寡糖和糖肽的融合合成。该程序为寡糖和带有炔烃侧链的肽的单锅水溶液连接提供了一种方法。

  DOI：

  10.1002/anie.201406694

文献信息

• Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates
  作者：Antony J. Fairbanks

  DOI：10.1016/j.carres.2020.108197

  日期：2021.1

  its derivatives are useful for numerous synthetic transformations in which the anomeric centre of unprotected reducing sugars is selectively activated in aqueous solution. As such unprotected sugars can undergo anomeric substitution with a range of added nucleophiles, providing highly efficient routes to a range of glycosides and glycoconjugates without the need for traditional protecting group manipulations

  2-氯-1,3-二甲基咪唑啉氯化物（DMC，本文也称为 Shoda 试剂）及其衍生物可用于许多合成转化，其中未保护的还原糖的异头中心在水溶液中被选择性激活。由于此类未受保护的糖可以用一系列添加的亲核试剂进行异头取代，从而为一系列糖苷和糖缀合物提供高效途径，而无需进行传统的保护基操作。这篇简短的评论总结了 DMC 及其一些衍生物/类似物的发展，并重点介绍了保护无基团合成的最新应用。
• One-step conversion of unprotected sugars to β-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution
  作者：Tomonari Tanaka、Hikaru Nagai、Masato Noguchi、Atsushi Kobayashi、Shin-ichiro Shoda

  DOI：10.1039/b905761g

  日期：——

  Various β-glycosyl azides have been synthesized directly in water by the reaction of unprotected sugars and sodium azide mediated by 2-chloro-1,3-dimethylimidazolinium chloride (DMC).

  在 2-氯-1,3-二甲基氯化咪唑啉（DMC）的介导下，通过非保护糖和叠氮化钠的反应，在水中直接合成了各种δ-糖基叠氮化物。
• One-Pot Conversion of Free Sialoglycans to Functionalized Glycan Oxazolines and Efficient Synthesis of Homogeneous Antibody–Drug Conjugates through Site-Specific Chemoenzymatic Glycan Remodeling
  作者：Chong Ou、Chao Li、Roushu Zhang、Qiang Yang、Guanghui Zong、Yuanwei Dai、Rebecca L. Francis、Stylianos Bournazos、Jeffrey V. Ravetch、Lai-Xi Wang

  DOI：10.1021/acs.bioconjchem.1c00314

  日期：2021.8.18

  oxazolines and a much shorter reaction time than that of the Endo-S D233Q-catalyzed reaction, thus minimizing the side reactions. Finally homogeneous ADCs were constructed with three different click reactions. The resulting ADCs showed excellent serum stability, and in vitro cytotoxicity assays indicated that all the three ADCs generated from the distinct click reactions possessed potent and comparable cytotoxicity

  抗体-药物偶联物 (ADC) 是一类重要的治疗药物，它利用抗体的高度特异性抗原靶向特性来递送用于靶向细胞杀伤的毒性药物。位点特异性偶联方法对于构建具有明确的抗体与药物比率、稳定性、理想的药理学特征和最佳治疗指数的均质 ADC 是非常可取的。我们在此报告了一种从游离唾液酸聚糖轻松合成功能化聚糖恶唑啉的方法，这些唾液酸聚糖是酶促 Fc 聚糖重塑的关键供体底物，以及应用高效的内切糖苷酶突变体 (Endo-S2 D184M) 进行位点特异性聚糖转移以构建同质 ADC。我们发现，通过在优化条件下连续使用两种偶联剂，游离唾液聚糖可以有效地转化为选择性功能化的聚糖恶唑啉，分别带有叠氮化物、环丙烯和降冰片烯标签，产率高且简单的一锅法。我们进一步证明，最近报道的 Endo-S2 D184 M 突变体对于 Fc 聚糖重塑非常有效，它使用选择性修饰的聚糖恶唑啉将标签引入抗体，这需要显着更少量的聚糖恶唑啉和更短的反应时间。
• Efficient Synthesis of Sugar Oxazolines from Unprotected <i>N</i>-Acetyl-2-amino Sugars by Using Chloroformamidinium Reagent in Water
  作者：Masato Noguchi、Tomonari Tanaka、Hidetoshi Gyakushi、Atsushi Kobayashi、Shin-ichiro Shoda

  DOI：10.1021/jo8024708

  日期：2009.3.6

  Sugar oxazoline derivatives were directly synthesized from the corresponding N-acetyl-2-amino sugars in aqueous media by using a chloroformamidinium-type dehydrating reagent. The present method could successfully be applied to chito-oligosaccharides, saccharides with acid functions, and a complex-type oligosaccharide derived from a glycopeptide.
• Protecting-Group-Free One-Pot Synthesis of Glycoconjugates Directly from Reducing Sugars
  作者：David Lim、Margaret A. Brimble、Renata Kowalczyk、Andrew J. A. Watson、Antony John Fairbanks

  DOI：10.1002/anie.201406694

  日期：2014.10.27

  The conversion of sugars into glycomimetics typically involves multiple protecting‐group manipulations. The development of methodology allowing the direct aqueous conversion of free sugars into glycosides, and mimics of oligosaccharides and glycoconjugates in a high‐yielding and stereoselective process is highly desirable. The combined use of 2‐azido‐1,3‐dimethylimidazolinium hexafluorophosphate and

  糖类转化为拟糖模拟物通常涉及多个保护基团操纵。迫切需要开发一种方法，以将高糖和立体选择性过程中的游离糖直接水转化为糖苷，并模拟寡糖和糖缀合物。六氟磷酸2-叠氮基-1,3-二甲基咪唑啉鎓与Cu催化的Huisgen环加成反应的结合使用，可以直接在含水条件下通过还原糖在一步反应中合成一系列糖结合物。该反应是完全立体选择性的，可用于三唑连接的糖苷，寡糖和糖肽的融合合成。该程序为寡糖和带有炔烃侧链的肽的单锅水溶液连接提供了一种方法。