1,2,3,4-tetra-O-butyryl-D-glucopyranose

• 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: 1,2,3,4-tetra-O-butyryl-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R)-4,5,6-tri(butanoyloxy)-2-(hydroxymethyl)tetrahydropyran-3-yl] butanoate；1,2,3,4-tetra-O-butyryl-α,β-D-glucopyranose；[(2R,3R,4S,5R)-4,5,6-tri(butanoyloxy)-2-(hydroxymethyl)oxan-3-yl] butanoate
• 化学式: C₂₂H₃₆O₁₀
• 分子量: 460.522
• InChiKey: IPFIZBKAEVGEQF-JKROVHOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  富马酸单甲酯 、 1,2,3,4-tetra-O-butyryl-D-glucopyranose 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 以900 mg的产率得到methyl (((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis(butyryloxy)tetrahydro-2H-pyran-2-yl)methyl) fumarate
  参考文献：
  名称：

  [EN] MONOMETHYL FUMARATE-CARRIER CONJUGATES AND METHODS OF THEIR USE
  [FR] CONJUGUÉS DE MONOMÉTHYL FUMARATE ET D'UN PORTEUR ET LEURS MÉTHODES D'UTILISATION

  摘要：

  公开号：

  WO2020118178A8
• 作为产物：
  描述：

  [(2R,3R,4S,5R)-4,5,6-tri(butanoyloxy)-2-(trityloxymethyl)tetrahydropyran-3-yl] butanoate 在 氢溴酸 、 溶剂黄146 作用下， 反应 0.5h， 以47.69%的产率得到1,2,3,4-tetra-O-butyryl-D-glucopyranose
  参考文献：
  名称：

  [EN] MONOMETHYL FUMARATE-CARRIER CONJUGATES AND METHODS OF THEIR USE
  [FR] CONJUGUÉS DE MONOMÉTHYL FUMARATE ET D'UN PORTEUR ET LEURS MÉTHODES D'UTILISATION

  摘要：

  公开号：

  WO2020118178A8

文献信息

• Synthetic study on neoponkoranol and its side chain epimer as potent α-glucosidase inhibitors, optimization of protecting group
  作者：Dan Liu、Weijia Xie、Long Liu、Hequan Yao、Jinyi Xu、Genzoh Tanabe、Osamu Muraoka、Xiaoming Wu

  DOI：10.1016/j.tetlet.2013.09.044

  日期：2013.11

  Coupling reaction between thiosugar and triflate as the key protocol to synthesize neoponkoranol, a naturally occurring potent α-glucosidase inhibitor, and its related sulfonium salts was optimized by applying different esters as protecting group, with the yields of desired products being greatly improved. Our proposed mechanism of the coupling reaction indicated that the nucleophilicity of C3-hydroxyl

  硫糖与三氟甲磺酸酯之间的偶联反应是合成天然有效的α-葡萄糖苷酶抑制剂新ponkoranol及其相关sulf盐的关键方法，通过使用不同的酯作为保护基，可以大大提高所需产物的收率。我们提出的偶联反应机理表明，C3-羟基部分在单糖结构上的亲核性与反应模式密切相关。
• Design, Synthesis, and Biological Evaluation of Novel Carbohydrate-Based Sulfamates as Carbonic Anhydrase Inhibitors
  作者：Marie Lopez、Jonathan Trajkovic、Laurent F. Bornaghi、Alessio Innocenti、Daniela Vullo、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm101525j

  日期：2011.3.10

  Carbonic anhydrases (CAs) IX and XII are enzymes with newly validated potential for the development of personalized, first-in-class cancer chemotherapies. Here we present the design and synthesis of novel carbohydrate-based CA inhibitors, several of which were very efficient inhibitors (K-i < 10 nM) with good selectivity for cancer-associated CA isozymes over off-target CA isozymes. All inhibitors comprised a carbohydrate core with one hydroxyl group derivatized as a sulfamate. Five different carbohydrates were chosen to present a selection of molecular shapes with subtle stereochernical differences to the CA enzymes active site. Variable modifications of the remaining sugar hydroxyl groups were incorporated to provide an incremental coverage of chemical property parameters that are associated with biopharmaceutical performance. All sulfamate inhibitors displayed ligand efficiencies that are consistent with those reported for good drug lead candidates.
• MONOMETHYL FUMARATE-CARRIER CONJUGATES AND METHODS OF THEIR USE
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：EP3890721A1

  公开（公告）日：2021-10-13
• [EN] MONOMETHYL FUMARATE-CARRIER CONJUGATES AND METHODS OF THEIR USE<br/>[FR] CONJUGUÉS DE MONOMÉTHYL FUMARATE ET D'UN PORTEUR ET LEURS MÉTHODES D'UTILISATION
  申请人：FLAGSHIP PIONEERING INNOVATIONS V INC

  公开号：WO2020118178A8

  公开（公告）日：2020-07-16