1-O-(4′-fluorophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 50819-49-3

• 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-O-(4′-fluorophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: (4-Fluorophenyl)-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-fluorophenoxy)oxan-2-yl]methyl acetate
• CAS: 50819-49-3
• 化学式: C₂₀H₂₃FO₁₀
• 分子量: 442.395
• InChiKey: SRBZWSJNBBJVKY-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  11

反应信息

• 作为产物：
  描述：

  4-氟苯酚 、 β-D-葡萄糖五乙酸酯 在 H-β-zeolite 作用下， 以38%的产率得到1-O-(4′-fluorophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective single-step synthesis and X-ray crystallographic investigation of acetylated aryl 1,2-trans glycopyranosides and aryl 1,2-cis C2-hydroxy-glycopyranosides

  摘要：

  Reported is an attractive and environmentally friendly method for the synthesis of the title compounds in moderate yield using inexpensive 1,2,3,4,6-penta-O-acetyl-beta-D-gluco- and galactopyranoses as sugar donors, five different phenols as acceptors and H-beta zeolite as the catalyst. The yield (23-28%) of aryl 3,4,6-tri-O-acetyl-alpha-D-glycopyranosides obtained in this single-step procedure is considerably higher than that obtained using previously reported methods. Treatment of an orthoacetate, 3,4,6-tri-O-acetyl-[1,2-O-(1-p-fluorophenoxyethylidene)]-alpha-D-glucopyranose, with p-fluorophenol under the same solvent-free reaction conditions also led to the formation of the title compounds in similar yield and composition. X-ray crystallographic analysis of phenyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside and p-fluorophenyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside showed that the molecular packing is stabilized by C-H center dot center dot center dot O, C-H center dot center dot center dot pi and C-H center dot center dot center dot F interactions, in addition to regular hydrogen bonding patterns. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.10.010

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。
• GLYCOSYLTRANSFERASE REVERSIBILITY FOR SUGAR NUCLEOTIDE SYNTHESIS AND MICROSCALE SCANNING
  申请人：Thorson Jon S.

  公开号：US20130004979A1

  公开（公告）日：2013-01-03

  The present invention generally relates to materials and methods for exploiting glycosyltransferase reversibility for nucleotide diphosphate (NDP) sugar synthesis. The present invention provides engineered glycosyltransferase enzymes characterized by improved reaction reversibility and expanded sugar donor specificity as compared to corresponding non-mutated glycosyltransferase enzymes. Such reagents provide advantageous routes to NDP sugars for subsequent use in a variety of biomedical applications, including enzymatic and chemo-enzymatic glycorandomization.

  本发明一般涉及利用糖基转移酶可逆性合成核苷酸二磷酸（NDP）糖的材料和方法。本发明提供了改良反应可逆性并扩展糖供体特异性的工程糖基转移酶酶，与相应的非突变糖基转移酶酶相比，具有更好的反应可逆性和扩展的糖供体特异性。这些试剂提供了有利的NDP糖路线，用于随后在各种生物医学应用中使用，包括酶促和化学酶促糖随机化。