tris-(O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)hydroxymethyl)-N-(benzyloxycarbonyl)glycyl aminomethane | 91202-75-4

• 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: tris-(O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)hydroxymethyl)-N-(benzyloxycarbonyl)glycyl aminomethane
• 英文别名: N-methyl>methyl>-N^α-(benzyloxycarbonyl)glycinamide；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxymethyl]propoxy]oxan-2-yl]methyl acetate
• CAS: 91202-75-4
• 化学式: C₅₆H₇₄N₂O₃₃
• 分子量: 1303.2
• InChiKey: YQUNSCCASSZPIC-GZRKGJNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  91
• 可旋转键数：
  42
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  438
• 氢给体数：
  2
• 氢受体数：
  33

反应信息

• 作为反应物：
  描述：

  tris-(O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)hydroxymethyl)-N-(benzyloxycarbonyl)glycyl aminomethane 生成 2-amino-N-[1,3-bis[[(2R,3R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-2-[[(2R,3R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]propan-2-yl]acetamide
  参考文献：
  名称：

  KEMPEN, HERMANUS J. M.

  摘要：

  DOI：
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 水 、 氰化汞 、 乙酸酐 、 三溴化磷 、 mercury dibromide 作用下， 以 乙腈 为溶剂， 生成 tris-(O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)hydroxymethyl)-N-(benzyloxycarbonyl)glycyl aminomethane
  参考文献：
  名称：

  A water-soluble cholesteryl-containing Tris-galactoside: synthesis, properties, and use in directing lipid-containing particles to the liver

  摘要：

  The synthesis of a trisgalactoside-terminated cholesterol derivative is described. Tris(galactosyloxymethyl)-aminomethane is coupled to cholesterol by using glycyl and succinyl as intermediate hydrophilic spacer moieties. The resulting cholesteryl ester dissolves easily in water, forming monodisperse micelles. When added to dispersions of liposomes or plasma lipoproteins in water, the substance becomes incorporated rapidly into these structures, causing an increase of their buoyant density. Liposomes or low-density lipoproteins, preloaded with the substance, are rapidly cleared from the circulation and taken up by the liver after intravenous injection in rats. This uptake is inhibited by N-acetylgalactosamine but not by N-acetylglucosamine, indicating the specificity of this process.

  DOI：

  10.1021/jm00376a014

文献信息

• 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.
• Synthèse de glycolipides polymérisables Dérivés du Tris(hydroxyméthyl)aminométhane: Préparation de micelles polymérisées.
  作者：B. Pucci、A. Polidori、N. Rakotomanomana、M. Chorro、A.A. Pavia

  DOI：10.1016/s0040-4039(00)60523-3

  日期：1993.6

  We have synthesized a series of new polymerizable glycolipids derived from Tris(hydroxymethyl) aminomethane (TRIS). Galactosylation of TRIS was performed in good yield by means of ultrasounds. Polymerization of 11-N-acrylamido-N-Tris(beta-D-galactopyranosyl oxymethyl)methyl undecanamide in aqueous solution by UV irradiation, led to polymerized micellar structures (A).
• DUDUKINA, T. V.;NEPOGODEV, S. A.;BELENKIJ, D. M., BIOXIMIYA, 55,(1990) N, S. 1474-1480
  作者：DUDUKINA, T. V.、NEPOGODEV, S. A.、BELENKIJ, D. M.

  DOI：——

  日期：——