N-succinimidyl benzyloxyacetate | 71624-31-2

• 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: N-succinimidyl benzyloxyacetate
• 英文别名: N-succinimidyl-2-benzyloxylacetate；O-benzylglycolic acid succinimidyl ester；BnOCH2COONSu；N-succinimidyl-O-benzylglycolate；(2,5-Dioxopyrrolidin-1-yl) 2-phenylmethoxyacetate
• CAS: 71624-31-2
• 化学式: C₁₃H₁₃NO₅
• 分子量: 263.25
• InChiKey: ZVVBGBFRSXLCEF-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C
• 沸点：
  382.4±44.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-succinimidyl benzyloxyacetate 在 sodium azide 、 甲烷磺酸 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三苯基膦 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.01h， 生成
  参考文献：
  名称：

  Design, synthesis and molecular docking study of α-triazolylsialosides as non-hydrolyzable and potent CD22 ligands

  摘要：

  Ligand 1 was the first reported example of monomeric high-affinity synthetic CD22 ligand that regulated B cell activation in vitro, augmented antibody production and regulated immune responses in mice. Replacing O-glycoside linkage of 1 by nitrogen of triazole by click reaction afforded compounds which are as potent as the parent compound. The synthesis of the new compounds is straightforward with fewer synthetic steps and higher yield. Such a strategy provided stable ligand that can bind avidly and can be conjugated to drugs for B-cell targeting or multimeric formation. The new compounds were screened for their affinity to CD22, using surface plasmon resonance (SPR). Compound 12 was obtained as a bioisosteric analogue and an anomerically stable imitation of 1. It was, also, screened for MAG to test for selectivity and analyzed by molecular docking and dynamic simulation to explore the potential binding modes and source of selectivity within CD22. Our results could enable the development of small molecule drug capable of modulating the activity of CD22 in autoimmune diseases and malignancies derived from B-cells.

  DOI：

  10.1016/j.ejmech.2020.112707
• 作为产物：
  描述：

  N,N'-二琥珀酰亚胺基碳酸酯 、 乙醇酸苯甲酯 在 吡啶 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 生成 N-succinimidyl benzyloxyacetate
  参考文献：
  名称：

  N-glycolylneuraminic acid derivative

  摘要：

  这项发明提供了一个具有以下式子的新化合物：##STR1## 这个化合物是制备N-乙二醇基神经酰胺酸的有用中间体：##STR2##

  公开号：

  US04774327A1

文献信息

• Synthesis of Diverse<i>N</i>-Substituted Muramyl Dipeptide Derivatives and Their Use in a Study of Human NOD2 Stimulation Activity
  作者：Kuo-Ting Chen、Duen-Yi Huang、Cheng-Hsin Chiu、Wan-Wan Lin、Pi-Hui Liang、Wei-Chieh Cheng

  DOI：10.1002/chem.201501557

  日期：2015.8.17

  preparation of diverse N‐substituted muramyl dipeptides (N‐substituted MDPs) from different protected monosaccharides is described. The synthetic MDPs include N‐acetyl MDP and N‐glycolyl MDP, known NOD2 ligands, and this methodology allows for structural variation at six positions, including the muramic acid, peptide, and N‐substituted moieties. The capacity of these molecules to activate human NOD2 in the

  描述了一种灵活的合成策略，该策略可从不同的受保护单糖制备各种N-取代的戊二酰二肽（N-取代的MDP）。合成的MDP包括已知的NOD2配体N-乙酰基MDP和N-甘氨酰基MDP，这种方法允许在六个位置上进行结构变异，包括山mic酸，肽和N-取代的部分。还研究了这些分子在先天免疫应答中激活人NOD2的能力。结果发现，在N-甘氨酰MDP的C 1位置添加甲基显着增强了NOD2的刺激活性。
• A Divergent Method to Prepare 5-Amino-, 5-<i>N</i>-Acetamido-, and 5-<i>N</i>-Glycolylsialosides
  作者：Thomas J. Boltje、Torben Heise、Floris P. J. T. Rutjes、Floris L. van Delft

  DOI：10.1002/ejoc.201300664

  日期：2013.8

  (non-human), or amine (cancer associated) functionality. Access to homogeneous sialosides with distinct substitution patterns is essential to determine structure–activity relationships. Herein, we report a divergent chemical approach to enable the synthesis of a library of specifically substituted sialosides by using a single sialic acid building block.

  唾液酸是涉及碳水化合物识别的生物过程的重要介质。唾液酸识别的主要决定因素是 N-5 取代基，它可以是 N-乙酰基（人）、N-羟乙酰（非人）或胺（癌症相关）功能。获得具有不同取代模式的均质唾液酸对于确定结构-活性关系至关重要。在此，我们报告了一种不同的化学方法，可以通过使用单个唾液酸构建块来合成特定取代的唾液酸苷库。
• Facile anomer-oriented syntheses of 4-methylumbelliferyl sialic acid glycosides
  作者：Abdullah A. Hassan、Stefan Oscarson

  DOI：10.1039/d1ob00877c

  日期：——

  reaction of iodine and the aglycone to the corresponding glycal followed by reduction of the resulting 3-iodo compounds. Both anomer-oriented synthetic pathways allow for gram-scale stereoselective syntheses of the desired C-5 modified neuraminic acid derivatives for use as tools to quantify the enzymatic activity and substrate specificity of known sialidases, and potential detection and investigation

  作为寻找新唾液酸酶并确定其酶特异性和催化活性的计划的一部分，从N-乙酰神经氨酸制备了在 C-5 位置衍生的 4-甲基伞形酮唾液酸糖苷文库。α-和β-4-甲基伞形酮唾液酸糖苷均以高产率和立体选择性制备。α-异头物通过使用添加剂 CH 3的试剂控制获得CN 和 TBAI，而 β-异头异构体是通过碘和苷元与相应的糖醛的非对映选择性加成反应，然后还原所得的 3-碘化合物来合成的。两种面向异头异构体的合成途径都允许对所需的 C-5 修饰的神经氨酸衍生物进行克级立体选择性合成，用作量化已知唾液酸酶的酶活性和底物特异性的工具，以及对新型唾液酸酶的潜在检测和研究。
• Synthesis of N-Glycolyl-8-O-sulfoneuraminic Acid.
  作者：Makoto TANAKA、Toshitsugu KAI、Xue-Long SUN、Hiroaki TAKAYANAGI、Kimio FURUHATA

  DOI：10.1248/cpb.43.2095

  日期：——

  N-Glycolyl-8-O-sulfoneuraminic acid (1) was synthesized for the first time in good yield. The key intermediates for synthesis of 1, neuraminic acid O-benzyl α-glycoside (3) and neuraminic acid S-methyl α-glycoside (10) were prepared from readily available N-acetylneuraminic acid. The structures of these compounds were confirmed by analysis of their NMR spectra.

  首次合成了 N-乙酰基-8-O-砜基神经氨酸（1），收率良好。合成 1 的关键中间体神经氨酸 O-苄基 α-糖苷（3）和神经氨酸 S-甲基 α-糖苷（10）是用容易获得的 N-乙酰神经氨酸制备的。通过分析这些化合物的核磁共振光谱，确认了它们的结构。
• A facile preparation of the methyl 2-thioglycoside of N-glycolylneuraminic acid, an efficient donor of NeuGc
  作者：Tetsuji Sugata、Ryuichi Higuchi

  DOI：10.1016/0040-4039(96)00383-8

  日期：1996.4

  The methyl 2-thioglycoside of N-glycolylneuraminic acid (SMe-NeuGc, 1), which is an efficient donor of NeuGc in the preparation of sialosyl glycoconjugates, was synthesized from N-acetylneuraminic acid (NeuAc) in 6 steps in good yield. 1 could be glycosylated with two lactose acceptors to give sialosyl oligosaccharides 8, 9 and 10 in high yields.

  由N-乙酰神经氨酸（NeuAc）分6步合成N-乙酰神经氨酸（SMe-NeuGc，1）的甲基2-硫代糖苷（SMe-NeuGc，1），它是NeuGc在制备唾液酸糖结合物中的有效供体。1可以用两个乳糖受体糖基化以高产率得到唾液酸寡糖8、9和10。