1,2,3,4-tetra-O-benzoyl-β-L-fucopyranose

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,4-tetra-O-benzoyl-β-L-fucopyranose
• 英文别名: [(2S,3R,4R,5S,6R)-4,5,6-tribenzoyloxy-2-methyloxan-3-yl] benzoate
• 化学式: C₃₄H₂₈O₉
• 分子量: 580.591
• InChiKey: RLJCRSFLYYQNAK-CIPFRLLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  6-deoxy-L-galactose 、 苯甲酰氯 在 吡啶 作用下， 反应 3.0h， 生成 1,2,3,4-tetra-O-benzoyl-β-L-fucopyranose 、 1,2,3,4-tetra-O-benzoyl-α-L-fucopyranoside
  参考文献：
  名称：

  糖-1-磷酸的立体定向合成及其向糖核苷酸的转化。

  摘要：

  随着Leloir糖基转移酶越来越多地用于制备寡糖，糖结合物和糖基化天然产物，需要有效地获得立体纯糖核苷酸供体底物。本文中，通过用三氟乙酸酐和N-甲基咪唑将带有嘌呤和嘧啶碱基的核苷5'-单磷酸核苷轻松活化30分钟，然后与立体定向制备的糖-1偶联2小时，从而快速合成和纯化八个糖核苷酸-磷酸盐。碳酸氢三丁铵和乙酸三丁铵是分别用于6-脱氧糖核苷酸和己糖或戊糖衍生糖核苷酸的C18反相纯化的离子对试剂。

  DOI：

  10.1016/j.carres.2008.01.046

文献信息

• On-Chip Screening of a Glycomimetic Library with C-Type Lectins Reveals Structural Features Responsible for Preferential Binding of Dectin-2 over DC-SIGN/R and Langerin
  作者：Laura Medve、Silvia Achilli、Sonia Serna、Fabio Zuccotto、Norbert Varga、Michel Thépaut、Monica Civera、Corinne Vivès、Franck Fieschi、Niels Reichardt、Anna Bernardi

  DOI：10.1002/chem.201802577

  日期：2018.9.25

  A library of mannose‐ and fucose‐based glycomimetics was synthesized and screened in a microarray format against a set of C‐type lectin receptors (CLRs) that included DC‐SIGN, DC‐SIGNR, langerin, and dectin‐2. Glycomimetic ligands able to interact with dectin‐2 were identified for the first time. Comparative analysis of binding profiles allowed their selectivity against other CLRs to be probed.

  合成了一个基于甘露糖和岩藻糖的糖模拟物库，并以微阵列格式针对一组包括DC-SIGN，DC-SIGNR，Langerin和dectin-2的C型凝集素受体（CLR）进行了筛选。首次鉴定出能够与dectin-2相互作用的拟模拟配体。结合概况的比较分析允许探测其对其他CLR的选择性。
• 1,2-<i>Trans</i>-Selective Synthesis of Glycosyl Boranophosphates and Their Utility as Building Blocks for the Synthesis of Phosphodiester-Linked Disaccharides
  作者：Kazuki Sato、Natsuhisa Oka、Shoichi Fujita、Fumiko Matsumura、Takeshi Wada

  DOI：10.1021/jo902725g

  日期：2010.4.2

  is controlled by neighboring group participation. The resultant glycosyl boranophosphate triesters were converted into the corresponding boranophosphate diesters and condensed with appropriately protected monosaccharides to give disaccharides linked with an anomeric boranophosphate linkage. Furthermore, the disaccharides worked as precursors of the corresponding phosphodiester-linked disaccharides

  高度1,2-反式通过二甲基硼酸磷酸酯与糖基碘化物的糖基化反应，开发了糖基硼酸磷酸酯衍生物的选择性合成方法。对反应机理的研究表明，反应的立体选择性受相邻基团的参与控制。将所得的糖基硼磷酸三酯转变为相应的硼磷酸二酯，并与适当保护的单糖缩合，得到与异头硼磷酸酯键连接的二糖。此外，二糖充当相应的磷酸二酯连接的二糖的前体。硼酸磷酸酯连接的二糖的完整合成及其向磷酸二酯连接的二糖的转化均以高收率完成，而在端基异构体位置没有损失立体纯度，
• Exploiting Nucleotidylyltransferases To Prepare Sugar Nucleotides
  作者：Shannon C. Timmons、Roy H. Mosher、Sheryl A. Knowles、David L. Jakeman

  DOI：10.1021/ol0630853

  日期：2007.3.1

  Enzymatic approaches to prepare sugar nucleotides are gaining in importance and offer several advantages over chemical synthesis including high yields and stereospecificity. We report the cloning, expression, and purification of two new wild-type thymidylyltransferases and observed catalysis with a wide variety of substrates. Significant product inhibition was not observed with the enzymes studied over a 24 h period, enabling the efficient preparation of 15 sugar nucleotides, clearly demonstrating the synthetic utility of these biocatalysts.
• Stereoselective Chemical Synthesis of Sugar Nucleotides via Direct Displacement of Acylated Glycosyl Bromides
  作者：Shannon C. Timmons、David L. Jakeman

  DOI：10.1021/ol063068d

  日期：2007.3.1

  The use of Leloir glycosyltransferases to prepare biologically relevant oligosaccharides and glycoconjugates requires access to sugar nucleoside diphosphates, which are notoriously difficult to efficiently synthesize and purify. We report a novel stereoselective route to UDP- and GDP-alpha-d-mannose as well as UDP- and GDP-beta-l-fucose via direct displacement of acylated glycosyl bromides with nucleoside 5'-diphosphates.