6-O-hexadecylsucrose | 187169-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-hexadecylsucrose
• 英文别名: (2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hexadecoxymethyl)oxane-3,4,5-triol
• CAS: 187169-00-2
• 化学式: C₂₈H₅₄O₁₁
• 分子量: 566.73
• InChiKey: AFCWVUQNMZREKA-SAXBRCJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  39
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-O-hexadecylsucrose 、 乙酸酐 以 吡啶 为溶剂， 反应 24.0h， 以80%的产率得到
  参考文献：
  名称：

  Synthesis of 6-O-Hexadecyl- and 6-O-Octylsucroses and Their Self-Assembling Properties Under Aqueous Conditions

  摘要：

  This paper reports the synthesis and self-assembling properties of 6-O-hexadecyl- and 6-O-octylsucroses. Mono-etherification of 2,3,4,1',3',4'-hexa-O-benzylsucrose with the corresponding alkyl bromides predominantly took place at the glucose 6-position and the products were isolated by silica gel column chromatography. Benzyl groups in the isolated products were cleaved to yield the target derivatives. The SEM, TEM, XRD, and DLS results indicated that 6-O-alkylsucroses formed vesicle-type particles via formation of lamellar-like planes under aqueous conditions, which were further merged by fusion of the planes to construct larger aggregates. The self-assembling properties of the materials were different from those of the previously reported 6-O- and 6'-O-hexadecylsucroses mixture.

  DOI：

  10.1080/07328303.2012.702250
• 作为产物：
  描述：

  1',2,3,3',4,4'-hexa-O-benzylsucrose 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 193.5h， 生成 6-O-hexadecylsucrose
  参考文献：
  名称：

  Synthesis of 6-O-Hexadecyl- and 6-O-Octylsucroses and Their Self-Assembling Properties Under Aqueous Conditions

  摘要：

  This paper reports the synthesis and self-assembling properties of 6-O-hexadecyl- and 6-O-octylsucroses. Mono-etherification of 2,3,4,1',3',4'-hexa-O-benzylsucrose with the corresponding alkyl bromides predominantly took place at the glucose 6-position and the products were isolated by silica gel column chromatography. Benzyl groups in the isolated products were cleaved to yield the target derivatives. The SEM, TEM, XRD, and DLS results indicated that 6-O-alkylsucroses formed vesicle-type particles via formation of lamellar-like planes under aqueous conditions, which were further merged by fusion of the planes to construct larger aggregates. The self-assembling properties of the materials were different from those of the previously reported 6-O- and 6'-O-hexadecylsucroses mixture.

  DOI：

  10.1080/07328303.2012.702250

文献信息

• Self-assembly of 6-O- and 6′-O-hexadecylsucroses mixture under aqueous conditions
  作者：Manami Kanemaru、Shin-ya Kuwahara、Kazuya Yamamoto、Yoshiro Kaneko、Jun-ichi Kadokawa

  DOI：10.1016/j.carres.2010.10.003

  日期：2010.12

  In this paper we report the self-assembly of 6-O- and 6'-O-hexadecylsucroses mixture under aqueous conditions The mixture was synthesized by a five-step sequence from sucrose The SEM image of a sample prepared by drying a dispersion of the mixture in water showed nanoparticles with the diameter of similar to 50 nm and aggregates that were formed by further assembly of them The XRD measurement of the sample exhibited the diffraction pattern assignable to face-centered cubic (FCC) structure and the diameter of a sphere which took part in the FCC structure was calculated to be 5 1 nm This value was relatively close to that observed in the DLS measurement of a dispersion of the mixture in water and estimated for a spherical micelle based on the molecular sizes of the two sucrose ethers On the basis of the above findings the following self-assembly process of the mixture under aqueous conditions was proposed The mixture formed the spherical micelles with the diameter of similar to 5-7 nm in water The micelles regularly organized according to the FCC structure during the drying process from the aqueous dispersion to construct the nanoparticles with the diameter of similar to 50 nm Several numbers of the nanoparticles further assembled to form the aggregates (C) 2010 Elsevier Ltd All rights reserved