3-O-stearoylsucrose

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 3-O-stearoylsucrose
• 英文别名: stearoyl(-3)Glc(a1-2b)Fruf；[(2R,3R,4S,5R,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] octadecanoate
• 化学式: C₃₀H₅₆O₁₂
• 分子量: 608.767
• InChiKey: WXTIRWRBFOPLQD-OSNHWPSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  42
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  硬脂酸酐 、 蔗糖 在 二正丁基氧化锡 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 99.0h， 以47%的产率得到β-D-fructofuranosyl 6-O-stearyl-α-D-glucopyranoside
  参考文献：
  名称：

  Regioselective Synthesis of Sucrose Monoesters as Surfactants

  摘要：

  A highly regioselective conversion of sucrose into 6-O-acyl derivatives is reported. First sucrose was transformed into the dibutyltin acetal, thus enhancing the nucleophilicity at the C-6 oxygen and restricting the subsequent acylation reaction. The surface activity properties of the sucrose monoesters obtained were determined and compared with those of commercially available ionic and non-ionic surfactants.

  DOI：

  10.1080/07328309708006506

文献信息

• Transesterification of Sucrose in Organic Medium: Study of Acyl Group Migrations
  作者：Valérie Molinier、Krzysztof Wisniewski、Alain Bouchu、Juliette Fitremann、Yves Queneau

  DOI：10.1081/car-120026466

  日期：2003.12.31

  of sucrose fatty acid esters to undergo intramolecular migrations in organic medium and the regioselectivity of some transesterifications of sucrose were investigated by HPLC, in situ NMR spectroscopy and preparative methods. Extensive acylation on secondary positions of the glucose moiety followed by migrations is general for base catalysed transesterification. The stability of 3‐ and 6‐O‐acyl derivatives

  通过HPLC，原位NMR光谱和制备方法研究了蔗糖脂肪酸酯的葡萄糖部分上的酰基在有机介质中发生分子内迁移的趋势以及一些蔗糖的酯交换反应的区域选择性。对于碱基催化的酯交换反应，通常在葡萄糖部分的次要位置上进行广泛的酰化，然后进行迁移。在一系列条件下研究了3-和6- O-酰基衍生物的稳定性，这两个异构体在热力学上比其他异构体更受青睐。结果表明，在有机碱性介质中，水的存在会催化OH-3处的酯向OH-6的迁移，而OH-6处的酯在酸性或碱性条件下显得更稳定。
• New highly regioselective reactions of unprotected sucrose. Synthesis of 2-O-acylsucroses and 2-O-(N-alkylcarbamoyl)sucroses
  作者：Caroline Chauvin、Krystyna Baczko、Daniel Plusquellec

  DOI：10.1021/jo00060a053

  日期：1993.4

  New methodologies which lead selectively to chosen regioisomeric mono-O-acylsucroses are described. The results indicate that a selective ionization of the free sugar makes the secondary 2-OH group of the glucose moiety more nucleophilic than the primary hydroxyls. New 2-O-acylsucroses 2 and 2-O-(N-alkylcarbamoyl)sucroses 3 were thus obtained in high yields.
• Regioselective Synthesis of Sucrose Monoesters as Surfactants
  作者：Iontcho Vlahov、Petinka Vlahova、Robert Linhardt

  DOI：10.1080/07328309708006506

  日期：1997.1.1

  A highly regioselective conversion of sucrose into 6-O-acyl derivatives is reported. First sucrose was transformed into the dibutyltin acetal, thus enhancing the nucleophilicity at the C-6 oxygen and restricting the subsequent acylation reaction. The surface activity properties of the sucrose monoesters obtained were determined and compared with those of commercially available ionic and non-ionic surfactants.