3-sucrose monooctanoate

• 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-sucrose monooctanoate
• 英文别名: 3-O-octanoylsucrose；3-N-Octanoylsucrose；[(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] octanoate
• 化学式: C₂₀H₃₆O₁₂
• 分子量: 468.499
• InChiKey: NMVDZWILYFXVBZ-PQJCEUABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  2,2,2-三氟乙基辛酸酯 、 蔗糖 在 proteinase N 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 生成 1'-sucrose monooctanoate 、 6'-sucrose monooctanoate 、 caprylic acid sucrose monoester 、 3-sucrose monooctanoate
  参考文献：
  名称：

  Proteinase N-catalysed regioselective esterification of sucrose and other mono- and disaccharides

  摘要：

  Crude Proteinase N was used as catalyst for the synthesis of carbohydrate (in particular sucrose) esters by transesterification of activated esters in organic solvents. Polymerisable or amphiphilic sucrose esters (methacrylates and laurates) were obtained regioselectively in good yields. The influence of the reaction parameters (temperature, pH, solvent, chain length, solid support) on the reaction rate, yield and selectivity was studied. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00424-4

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。
• Esterification of unprotected sucrose with acid chlorides in aqueous medium: kinetic reactivity versus acyl- or alkyloxycarbonyl-group migrations
  作者：Sophie Thévenet、Angelika Wernicke、Stanislaw Belniak、Gérard Descotes、Alain Bouchu、Yves Queneau

  DOI：10.1016/s0008-6215(99)00079-8

  日期：1999.5

  between formation, migration and hydrolysis of sucrose mono-esters and -carbonates confirmed that the pre-eminent reactivity of some secondary positions persists in aqueous medium, and in particular, OH-2, even though fast subsequent migrations finally enrich the mixture in compounds substituted at the primary positions. The reaction was also shown to depend strongly on the starting sucrose concentration

  摘要对蔗糖单酯和碳酸酯的形成，迁移和水解之间竞争的研究证实，即使在随后的快速迁移中，某些次要位置的反应仍在水性介质（尤其是OH-2）中持续存在。使混合物中的主要位置取代的化合物富集。与较小的链相比，在疏水性酰化剂的情况下，该反应还显示出强烈依赖于起始蔗糖的浓度，从而提供了更高的取代衍生物。
• Advanced drug development and manufacturing
  申请人：ICAGEN, LLC

  公开号：US10877035B2

  公开（公告）日：2020-12-29

  X-ray fluorescence (XRF) spectrometry has been used for detecting binding events and measuring binding selectivities between chemicals and receptors. XRF may also be used for estimating the therapeutic index of a chemical. For estimating the binding selectivities of a chemical versus chemical analogs, for measuring post translational modification of proteins, and for drug manufacturing.

  X 射线荧光 (XRF) 光谱法已被用于检测化学物质与受体之间的结合事件和测量结合选择性。XRF 还可用于估算化学品的治疗指数。XRF 还可用于估算化学品的治疗指数、估算化学品与化学类似物的结合选择性、测量蛋白质的翻译后修饰以及药物生产。
• X-ray microscope
  申请人：XRpro Sciences, Inc.

  公开号：EP2511844B1

  公开（公告）日：2015-08-12
• Advanced Drug Development and Manufacturing
  申请人：XRpro Sciences, Inc.

  公开号：US20150309021A1

  公开（公告）日：2015-10-29

  X-ray fluorescence (XRF) spectrometry has been used for detecting binding events and measuring binding selectivities between chemicals and receptors. XRF may also be used for estimating the therapeutic index of a chemical. For estimating the binding selectivities of a chemical versus chemical analogs, for measuring post translational modification of proteins, and for drug manufacturing.