Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[5-((S)-1-dihexadecylcarbamoyl-ethylcarbamoyl)-pentyloxy]-tetrahydro-pyran-4-yl ester | 195965-89-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[5-((S)-1-dihexadecylcarbamoyl-ethylcarbamoyl)-pentyloxy]-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[6-[[(2S)-1-(dihexadecylamino)-1-oxopropan-2-yl]amino]-6-oxohexoxy]oxan-2-yl]methyl acetate
• CAS: 195965-89-0
• 化学式: C₅₅H₁₀₀N₂O₁₂
• 分子量: 981.405
• InChiKey: ZTXPOZSSVPIQST-UJQUZMOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.94
• 重原子数：
  69.0
• 可旋转键数：
  44.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  173.07
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[5-((S)-1-dihexadecylcarbamoyl-ethylcarbamoyl)-pentyloxy]-tetrahydro-pyran-4-yl ester 在 肼 作用下， 以52%的产率得到6-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid ((S)-1-dihexadecylcarbamoyl-ethyl)-amide
  参考文献：
  名称：

  Preparation of Artificial Glycolipids and Their Aggregation Behavior in Aqueous Media

  摘要：

  N,N-Dihexadecyl-N-alpha-[6-(beta D-galactopyranosyl)hexanoyl]-L-alaninamide and N,N-dihexadecyl-N-alpha-[6-{(beta D-galactopyranosyl>(1 --> 4>O-(D-glucopyranosyl)}hexanoyl]-L-alaninamide, which have an amino acid residue interposed between a polar sugar moiety and a hydrophobic double-chain segment individually, were prepared and characterized as novel artificial glycolipids. Morphological studies by means of differential scanning calorimetry and dynamic light scattering as well as electron microscopy clarified that these lipids tend to form stable bilayer membranes by themselves in aqueous media. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01572-4
• 作为产物：
  描述：

  双十六烷基胺 在 四氯化锡 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 90.0h， 生成 Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[5-((S)-1-dihexadecylcarbamoyl-ethylcarbamoyl)-pentyloxy]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Preparation of Artificial Glycolipids and Their Aggregation Behavior in Aqueous Media

  摘要：

  N,N-Dihexadecyl-N-alpha-[6-(beta D-galactopyranosyl)hexanoyl]-L-alaninamide and N,N-dihexadecyl-N-alpha-[6-{(beta D-galactopyranosyl>(1 --> 4>O-(D-glucopyranosyl)}hexanoyl]-L-alaninamide, which have an amino acid residue interposed between a polar sugar moiety and a hydrophobic double-chain segment individually, were prepared and characterized as novel artificial glycolipids. Morphological studies by means of differential scanning calorimetry and dynamic light scattering as well as electron microscopy clarified that these lipids tend to form stable bilayer membranes by themselves in aqueous media. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01572-4