N-[tris[(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]methyl]glycinamide | 127619-24-3

• 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: N-[tris[(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]methyl]glycinamide
• 英文别名: N-glycinamid；tris(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxymethyl)methylamidoglycine
• CAS: 127619-24-3
• 化学式: C₄₈H₆₈N₂O₃₁
• 分子量: 1169.06
• InChiKey: VTAZDHUEODJIGY-AFMQTUAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  81.0
• 可旋转键数：
  26.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  426.1
• 氢给体数：
  2.0
• 氢受体数：
  32.0

反应信息

• 作为反应物：
  描述：

  N-[tris[(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]methyl]glycinamide 在 N,N'-二环己基碳二亚胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Synthesis of Glycodendrimers by Modification of Poly(propylene imine) Dendrimers

  摘要：

  AbstractThe use of preformed poly‐(propylene imine) dendrimers (DAB‐dendr‐(NH2)x) for the rapid and facile construction of high molecular weight carbohydrate‐coated dendrimers (glyco‐dendrimers) is presented. An efficient attachment of spacer‐armed derivatives of D‐galactose and lactose to the primary amino end groups of DAB‐dendr‐(NH2)x has been achieved by means of amide bond formation, using the N‐hydroxysuccinimide coupling procedure. Acetate protecting groups have been employed in order to avoid side reactions at the coupling stage. Deacetylation leads to the target glycodendrimers. The reactivity of all the available DAB‐dendr‐(NH2)x (generations 1–5) has been investigated and a series of homologous carbohydrate‐coated dendrimers have been synthesized. In addition, the attachment of larger saccharide moieties has been demonstrated by the condensation of a trisgalactoside cluster with DAB‐dendr‐(NH2)x carrying both four and eight primary amino groups. The regularity of the glycodendrimers has been proven by NMR spectroscopy, and the molecular weights of the low‐generation carbohydrate‐coated dendrimers have been determined by mass spectrometry. Modifications of DAB‐dendr‐(NH2)x with biologically active carbohydrates affords a new and simple approach to high molecular weight compounds that may be considered as neoglycoconjugates with perfectly symmetrical structures and that offer much promise as multivalent ligands involved in carbohydrate‐protein interactions.

  DOI：

  10.1002/chem.19970030620
• 作为产物：
  描述：

  N^α-<(9-Fluorenyl)methoxycarbonyl>-N-<2-hydroxy-1,1-bis(hydroxymethyl)ethyl>glycinamid 在 哌啶 、 氰化汞 、 mercury dibromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.5h， 生成 N-[tris[(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]methyl]glycinamide
  参考文献：
  名称：

  Peter, Martin G.; Boldt, Peter C.; Niederstein, Yvonne, Liebigs Annalen der Chemie, 1990, # 9, p. 863 - 869

  摘要：

  DOI：

文献信息

• Synthetic Gallic Acid Derivatives as Models for a Comprehensive Study of Antioxidant Activity
  作者：Florence Belin、Philippe Barthélémy、Karine Ruiz、Jean Michel Lacombe、Bernard Pucci

  DOI：10.1002/hlca.200390053

  日期：2003.2

  The synthesis and antioxidant efficiencies of amphiphilic gallic acid derivatives are reported. To specify the impact of chemical structure on the antioxidant efficiency, several structural modifications of gallic acid were performed. The following structural features were chosen: i) introduction of hydrophobic or hydrophilic residues on the gallic acid and the type of their linkage, ii) the hydrophilic

  报道了两亲没食子酸衍生物的合成和抗氧化剂效率。为了说明化学结构对抗氧化剂效率的影响，对没食子酸进行了几种结构修饰。选择了以下结构特征：i）在没食子酸上引入疏水或亲水残基以及它们的连接类型，ii）整个分子的亲水性和/或亲脂性。所制备的不同系列的理化研究表明，该多酚的抗氧化效率明显取决于与亲水和疏水部分的连接性质。始终需要推挽效应，酯或酰胺键似乎很适合提高抗氧化剂的效率。第二，观察到在所施加的氧化条件下，亲水性和/或亲脂性极大地影响了没食子酸衍生物的抗氧化活性。获得的结果与极性悖论相符，疏水性衍生物抑制了水相中的氧化，而亲水性产品则无效。
• A Strategy for the Targeting of Photosensitizers. Synthesis, Characterization, and Photobiological Property of Porphyrins Bearing Glycodendrimeric Moieties
  作者：Séverine Ballut、Delphine Naud-Martin、Bernard Loock、Philippe Maillard

  DOI：10.1021/jo102185d

  日期：2011.4.1

  This paper describes the conception, synthesis, and characterization of new tetrapyrrolic chromophores bearing glycodendrimeric moieties inducing a potential increase of tumor targeting by a cluster effect. Two families of monoglycodendrimeric photosensitizers bearing three glycosyl units were designed, prepared with an acceptable overall efficiency and characterized by NMR, UV-visible, and fluorescence spectroscopies. The polarity and log P were evaluated by HPLC and the stir-flask method, respectively. The in vitro photoefficiency against two human tumor cell lines was assessed. The presence of the glycodendrimeric group does not appear to increase the tumor in vitro targeting.
• Vesicles and other supramolecular systems made from double-tailed synthetic glycolipids derived from galactosylated tris(hydroxymethyl)aminomethane
  作者：Ange Polidori、Bernard Pucci、Leila Zarif、Jean-Michel Lacombe、Jean G. Riess、AndréA. Pavia

  DOI：10.1016/0009-3084(95)02475-x

  日期：1995.8

  A series of double-tailed hydrocarbon glycolipids derived from tris(hydroxymethyl)aminomethane (Tris) have been prepared. These amphiphiles consist of three parts: a hydrophilic head derived from mono- or polygalactosylated Tris, a linking arm of peptidic nature and a hydrophobic double tail composed of 12 or 18 carbon atom chains. The ability of the new glycolipids to disperse in water, the morphology of the self-assemblies they form and the stability of the latter were shown to depend largely on the volumetric ratio between hydrophilic head and hydrophobic tails. Comparative studies of such substrates allowed a better understanding of the relative role of the various parameters that govern the formation of tubular systems relative to vesicular organizations. In all cases, the introduction of oligomeric galactosylated heads favoured stable vesicular systems over tubules.
• Synthesis of double-chain glycolipids derived from aspartic acid : Preliminary investigation of their colloidal behavior
  作者：Ange Polidori、Bernard Pucci、Jean G. Riess、Leila Zarif、André A. Pavia

  DOI：10.1016/s0040-4039(00)76654-8

  日期：1994.5

  Double-tailed glycolipids derived from mono-, di- and tri-O-galactosyl tris-(hydroxymethyl) aminomethane and aspartic acid have been synthesized. Preliminary assessment by negative staining transmission electron microscopy of dispersions of these amphiphiles showed the formation of either vesicles, helical structures or fibers depending on the glycolipid structure.