but-3-ynyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside | 1313912-03-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: but-3-ynyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
• 英文别名: 2,3,4,6-tetra-O-acetyl-1-O-but-3-ynyl-α-D-galactopyranoside；2-butynyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(but-3-yn-1-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate；3-butynyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-but-3-ynoxyoxan-2-yl]methyl acetate
• CAS: 1313912-03-6
• 化学式: C₁₈H₂₄O₁₀
• 分子量: 400.383
• InChiKey: OYQAUEAPLXQJIA-DISONHOPSA-N

物化性质

• 沸点：
  458.9±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  but-3-ynyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 在 甲醇 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 sodium methylate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 1.17h， 生成 perfluorophenyl 1-(4-(2-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)ethyl)-1H-1,2,3-triazol-1-yl)-3,6,9,12-tetraoxapentadecan-15-oate
  参考文献：
  名称：

  [EN] HYPOIMMUNOGENIC BIOTHERAPEUTICS
  [FR] BIOTHÉRAPEUTIQUES HYPOIMMUNOGÈNES

  摘要：

  本公开提供了一种低免疫原性生物治疗组合物，可抑制个体对其产生免疫反应。本公开还提供了包含此类低免疫原性生物治疗剂的制药组合物，制备此类低免疫原性生物治疗剂的方法，以及将此类低免疫原性生物治疗剂用作治疗和研究的方法。

  公开号：

  WO2022150726A1
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 but-3-ynyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
  参考文献：
  名称：

  Multifunctional Surface Modification of Gold-Stabilized Nanoparticles by Bioorthogonal Reactions

  摘要：

  Nanocarriers that combine multiple properties in an all-in-one system hold great promise for drug delivery. The absence of technology to assemble highly functionalized devices has, however, hindered progress in nanomedicine. To address this deficiency, we have chemically synthesized poly(ethylene oxide)-beta-poly(epsilon-caprolactone) (PEO-b-PCL) block polymers modified at the apolar PCL terminus with thioctic acid and at the polar PEO terminus with an acylhydrazide, amine, or azide moiety. The resulting block polymers were employed to prepare nanoparticles that have a gold core, an apolar polyester layer for drug loading, a polar PEO corona to provide biocompatibility, and three different types of surface reactive groups for surface functionalization. The acylhydrazide, amine, or azide moieties of the resulting nanoparticles could be reacted with high efficiencies with modules having a ketone, isocyanate, or active ester and alkyne function, respectively. To demonstrate proof of principle of the potential of multisurface functionalization, we prepared nanoparticles that have various combinations of an oligo-arginine peptide to facilitate cellular uptake, a histidine-rich peptide to escape from lysosomes, and an Alexa Fluor 488 tag for imaging purposes. It has been shown that uptake and subcellular localization of the nanoparticles can be controlled by multisurface modification. It is to be expected that the modular synthetic methodology provides unique opportunities to establish optimal configurations of nanocarriers for disease-specific drug delivery.

  DOI：

  10.1021/ja2012164

文献信息

• Copper-catalyzed one-pot synthesis of glycosylated iminocoumarins and 3-triazolyl-2-iminocoumarins
  作者：Pintu Kumar Mandal

  DOI：10.1039/c3ra46844e

  日期：——

  general strategy was developed for the synthesis of glycosyl iminocoumarins (5a–x) in a one-pot, copper-catalyzed multicomponent reaction involving a domino reaction of sulfonyl azides, sugar alkynes, and salicylaldehydes via ketenimine intermediate formation. Similarly, glycosyl 3-triazolyl-2-iminocoumarin derivatives (6a–o) have also been synthesized in a one-pot, three component condensation via tandem

  已开发了在单罐，铜催化的多组分反应中合成糖基亚氨基香豆素（5a–x）的通用策略，该反应涉及通过乙炔亚胺中间体形成的磺酰叠氮化物，糖炔和水杨醛的多米诺反应。同样，糖基3-三唑基-2-亚氨基香豆素衍生物（6a-o）也已通过串联的“ CuAAC-醛醇-环化-脱水”序列以一锅，三组分缩合的方式合成。在这种情况下，2-叠氮基乙腈和糖炔之间的铜催化环加成反应可原位提供三唑衍生物。并活化了相邻的亚甲基，在水杨醛存在下诱导了羟醛-环化-脱水序列。在所有反应中收率都非常好。
• Orthogonal dual-modification of proteins for the engineering of multivalent protein scaffolds
  作者：Michaela Mühlberg、Michael G Hoesl、Christian Kuehne、Jens Dernedde、Nediljko Budisa、Christian P R Hackenberger

  DOI：10.3762/bjoc.11.88

  日期：——

  scaffold design, we have developed a novel dual-labeling strategy for proteins that combines residue-specific incorporation of unnatural amino acids with chemical oxidative aldehyde formation at the N-terminus of a protein. Our approach relies on the selective introduction of two different functional moieties in a protein by mutually orthogonal copper-catalyzed azide-alkyne cycloaddition (CuAAC) and oxime

  为了向基于蛋白质的多价支架设计添加新工具，我们开发了一种新颖的蛋白质双标记策略，该策略将非天然氨基酸的残基特异性掺入与蛋白质 N 末端的化学氧化醛形成结合起来。我们的方法依赖于通过相互正交的铜催化叠氮-炔环加成（CuAAC）和肟连接在蛋白质中选择性引入两个不同的功能部分。该方法应用于生物素和 β 连接半乳糖残基的缀合，产生具有酶活性的嗜热脂肪酶，通过 SPR 结合研究揭示了其与刺桐凝集素的特异性结合。
• Synthesis of saccharin-glycoconjugates targeting carbonic anhydrase using a one-pot cyclization/deprotection strategy
  作者：Akilah B. Murray、Marta Quadri、Haoxi Li、Robert McKenna、Nicole A. Horenstein

  DOI：10.1016/j.carres.2019.03.001

  日期：2019.4

  Simple cyclic sulfonamides, like saccharin (SAC), have shown up to a 60-fold selectivity towards CA IX over other ubiquitous CA isoforms, with greater selectivity obtained applying the "tail-approach" to derivatize SAC with a methylene triazole linker that connected to a "tail" beta glucoside. These modifications of SAC led to an increased selectivity of more than 1000-fold towards CA IX, whereas

  碳酸酐酶IX（CA IX）由于其在癌细胞生长和增殖中的作用而被确定为几种恶性肿瘤的生物标志物和药物靶标。简单的环状磺酰胺，如糖精（SAC），对CA IX的选择性比其他普遍存在的CA同工型高60倍，使用“尾巴法”通过与亚甲基三唑连接基衍生的SAC衍生化获得了更高的选择性。 “尾巴”β-葡萄糖苷。SAC的这些修饰导致对CA IX的选择性增加了1000倍以上，而临床上可用的CA抑制剂几乎没有或没有同种型选择性。作为开发新型CA抑制剂的兴趣之一，我们发现了现有的合成方案，该方案依赖于N-叔丁基糖精中间体，在最后的脱保护步骤中存在问题。因此，我们描述了合成这些化合物的另一种方法，其特征为轻柔的“一锅”脱保护/环化反应作为最终合成步骤，并报道了对CA IX具有低至中等nM抑制作用的新半乳糖基和葡萄糖基共轭物。
• Carreira Alkynylations with Paraformaldehyde. A Mild and Convenient Protocol for the Hydroxymethylation of Complex Base-Sensitive Terminal Acetylenes via Alkynylzinc Triflates
  作者：Karl J Hale、Ziyue Xiong、Liping Wang、Soraya Manaviazar、Ryan Mackle

  DOI：10.1021/ol503222j

  日期：2015.1.16

  A new synthetic protocol for the hydroxymethylation of terminal acetylenes is described that involves stoichiometric Carreira alkynylation with solid paraformaldehyde (HO[CH2O]nH) in PhMe at 60 °C. Significantly, the method can be successfully applied on acetylenes that possess base-sensitive ester functionality and heterocyclic rings that readily undergo metalation. While N-methylephedrine (NME) is generally the best Zn(OTf)2-coordinating ligand for promoting hydroxymethylation, TMEDA can serve as a replacement.