bis-(O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)hydroxymethyl)acetoxymethyl-N-(benzyloxycarbonyl)glycyl aminomethane | 151753-74-1

• 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: bis-(O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)hydroxymethyl)acetoxymethyl-N-(benzyloxycarbonyl)glycyl aminomethane
• CAS: 151753-74-1
• 化学式: C₄₄H₅₈N₂O₂₅
• 分子量: 1014.94
• InChiKey: OAYLKRUSVARAAD-FVTIPSFYSA-N

物化性质

• 沸点：
  955.5±65.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.47
• 重原子数：
  71.0
• 可旋转键数：
  23.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  341.05
• 氢给体数：
  2.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  bis-(O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)hydroxymethyl)acetoxymethyl-N-(benzyloxycarbonyl)glycyl aminomethane 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Synthesis of double-chain glycolipids derived from aspartic acid : Preliminary investigation of their colloidal behavior

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)76654-8
• 作为产物：
  描述：

  N-[1,1-bis(hydroxymethyl)-2-acetoxyethyl]-Nα-(benzyloxycarbonyl)glycinamide 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 氰化汞 作用下， 以 乙腈 为溶剂， 以72%的产率得到bis-(O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)hydroxymethyl)acetoxymethyl-N-(benzyloxycarbonyl)glycyl aminomethane
  参考文献：
  名称：

  Synthesis of double-chain glycolipids derived from aspartic acid : Preliminary investigation of their colloidal behavior

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)76654-8

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.
• 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).