3'-iodophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 903881-57-2

• 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: 3'-iodophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 1-O-(3′-iodophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(3-iodophenoxy)oxan-2-yl]methyl acetate
• CAS: 903881-57-2
• 化学式: C₂₀H₂₃IO₁₀
• 分子量: 550.301
• InChiKey: UQROLRGYPOCGNJ-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3'-iodophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 四(三苯基膦)钯 sodium methylate 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 21.5h， 生成 4-β-D-galactopyranosyl-3'-β-D-glucopyranosyl-biphenyl
  参考文献：
  名称：

  Antagonists of the myelin-associated glycoprotein: A new class of tetrasaccharide mimics

  摘要：

  The tetrasaccharide substructure 1 of the ganglioside GQ1b alpha shows a remarkable affinity for the myelin-associated glycoprotein (MAG). In the search for structurally simplified and pharmacokinetically improved mimics of 1, biphenyl was identified as a feasible replacement for the core disaccharide Ga1 beta(1-3)Ga1NAc according to saturation transfer difference (STD) NMR and molecular modeling investigations. Using Suzuki coupling, a convergent synthesis of the mimics was achieved. To optimize the yields of the coupling reactions, the catalytic effects of microwave irradiation and conventional heating were compared. The biological evaluation of mimics 3 and 4 was performed in a competitive target-based assay. It was found that the relative inhibitory potency (rIP) of antagonist 3 was clearly enhanced in comparison to the reference trisaccharide 2, despite the former having a much simpler structure. In addition to the improved synthetic feasibility, an increase of the partition coefficient between octanol and water (log P), and therefore a beneficial change in the pharmacokinetic properties of 3 and 4 was achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.007
• 作为产物：
  描述：

  3-碘苯酚 、 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到3'-iodophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  用糖基亚胺酯重新研究酚O-糖基化反应，BF3·OEt2是比TMSOTf更好的催化剂

  摘要：

  以BF（3）·OEt（2）为催化剂，苯酚与带有2-O-参与基团的糖基三氯乙酰基亚氨酸盐（或N-苯基三氟乙酰基亚氨酸盐）的糖基化反应通常会产生所需的1,2-反式-O-糖苷极佳的收率，而不会形成1,2-顺式端基异构体。然而，以TMSOTf为催化剂，相应的酚O-糖基化的结果高度依赖于酚的亲核性。苯酚的亲核性越少，生成的1，2-顺式-O-糖苷含量越高，副产物就越多。在所有这些酚O-糖基化反应中，发现1,2-原酸酯是低温（<-70°C）的主要产物，在较高温度下转化为最终产物。BF（3）·OEt（2）是促进1转化的有效催化剂 将2-原酸酯转化为相应的1，2-反式-O-糖苷。然而，在TMSOTf存在下，1,2-原酸酯可被转化为三氟甲磺酸二恶唑鎓和三氟甲磺酸糖基酯，这些中间体可能与糖基氧碳鎓相关物种处于平衡状态，最终形成α/β-O-的最终混合物。苷和副产物。

  DOI：

  10.1016/j.carres.2012.09.025

文献信息

• Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature
  作者：Tristan Verdelet、Sara Benmahdjoub、Belkacem Benmerad、Mouad Alami、Samir Messaoudi

  DOI：10.1021/acs.joc.9b01218

  日期：2019.7.19

  Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose

  已经建立了糖乳醇与取代的芳基硼酸的直接和实用的异头O-芳基化。在室温，空气气氛下使用铜催化，证明该方案是通用的，并且已经以良好至优异的产率制备了各种芳基O-糖苷。此外，该方法已成功地扩展到未保护的碳水化合物（包括α-甘露糖），并在此证明了碳水化合物和硼酸之间的相互作用如何与铜催化结合以实现选择性的异头O-芳基化。