methyl 3-O-benzoyl-α-L-arabinopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzoyl-α-L-arabinopyranoside
• 英文别名: [(2R,3R,4S,5S)-3,5-dihydroxy-2-methoxyoxan-4-yl] benzoate
• 化学式: C₁₃H₁₆O₆
• 分子量: 268.266
• InChiKey: MODPXXZTSFIZDO-SRRSOLGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲酰氯 、 甲基 alpha-L-阿拉伯吡喃糖苷 在 2,4,6-三甲基吡啶 、 bis(acetylacetonato)dioxidomolybdenum(VI) 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以81%的产率得到methyl 3-O-benzoyl-α-L-arabinopyranoside
  参考文献：
  名称：

  Regioselective Benzoylation of Glycopyranosides by Benzoyl Chloride in the Presence of MoO₂(acac)₂

  摘要：

  Benzoylation of methyl and benzyl glycopyranosides by benzoyl chloride in the presence of MoO2(acac)(2) as a catalyst resulted in 3-benzoates with good yield and high regioselectivity. Simple synthesis of the monobenzoates of some glycopyranosides is suggested.

  DOI：

  10.1080/07328303.2010.549258

文献信息

• Regioselective benzoylation of glycopyranosides by benzoic anhydride in the presence of Cu(CF3COO)2
  作者：Evgeny V. Evtushenko

  DOI：10.1016/j.carres.2012.06.020

  日期：2012.10

  Benzoylation of methyl and benzyl glycopyranosides by benzoic anhydride in acetonitrile in the presence of copper(II) trifluoroacetate as a promoter has given monobenzoates with a good yield and high regioselectivity. The composition of monobenzoates depended both on a configuration of hydroxyl groups and on a configuration of aglycone. The simple syntheses of the monobenzoates of some glycosides are

  在三氟乙酸铜（II）作为促进剂的存在下，在乙腈中通过苯甲酸酐在苯甲腈中对甲基和苄基吡喃葡萄糖苷进行苯甲酰化，得到了单苯甲酸酯，具有良好的收率和较高的区域选择性。单苯甲酸酯的组成取决于羟基的构型和糖苷配基的构型。提供了一些糖苷的单苯甲酸酯的简单合成。
• Conformational equilibria of methyl α-<scp>L</scp>-arabinopyranosides in solution
  作者：Rosa Lanzetta、Michelangelo Parrilli、Carmine Garzillo、Andrea di Matteo、Giuseppe del Re

  DOI：10.1039/p29960000505

  日期：——

  except in the case of 2-substituted derivatives in CDCl3. The experimental data and a theoretical analysis aimed at explaining them in terms of intramolecular and stereoelectronic solvent effects are presented. It appears that certain electrostatic interactions and the anomeric effect, which favour 1C4 in conformational equilibria are particularly important in 2-substituted derivatives provided no

  对CDCl 3中的甲基α- L-阿拉伯吡喃糖苷，吡啶和二恶烷进行的NMR实验研究表明，除了CDCl 3中有2个取代的衍生物外，构象异构体之间的平衡也朝着4 C 1构象异构体转移。提出了实验数据和旨在从分子内和立体电子溶剂效应方面解释它们的理论分析。看来，某些静电相互作用和端基异构作用有利于1 C 4。如果不破坏分子内H-桥，则构象平衡中的构象平衡在2-取代的衍生物中特别重要。这解释了实验结果，并进一步阐明了决定溶液中构象平衡的效应之间的相互作用。
• Regioselective Benzoylation of Glycopyranosides by Benzoyl Chloride in the Presence of MoO₂(acac)₂
  作者：E. V. Evtushenko

  DOI：10.1080/07328303.2010.549258

  日期：2010.11.1

  Benzoylation of methyl and benzyl glycopyranosides by benzoyl chloride in the presence of MoO2(acac)(2) as a catalyst resulted in 3-benzoates with good yield and high regioselectivity. Simple synthesis of the monobenzoates of some glycopyranosides is suggested.