methyl 3-O-methyl-α-D-arabinofuranoside | 60738-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-methyl-α-D-arabinofuranoside
• 英文别名: (2S,3S,4S,5R)-5-(hydroxymethyl)-2,4-dimethoxyoxolan-3-ol
• CAS: 60738-01-4
• 化学式: C₇H₁₄O₅
• 分子量: 178.185
• InChiKey: YGAVQJVFQKBFHL-UCROKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-O-methyl-α-D-arabinofuranoside 在 吡啶 、 硫酸 作用下， 反应 1.0h， 生成 1,2,5-tri-O-acetyl-3-O-methyl-D-arabinofuranose
  参考文献：
  名称：

  Oligosaccharides as inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-3 modified arabinofuranosyl residues

  摘要：

  The assembly of the arabinan portions of cell wall polysaccharicles in mycobacteria involves a family of arabinosyltransferases (AraT's) that promote the polymerization of decaprenolphosphoarabinose. Mycobacterial viability depends upon the ability of the organism to synthesize an intact arabinan and thus compounds that inhibit these AraT's are both useful biochemical tools as well as potential lead compounds for new anti-tuberculosis agents. We describe here the preparation of oligosaccharide fragments of mycobacterial arabinan that contain arabinofuranosyl residues modified at C-3 by the replacement of the hydroxyl group with an amino, azido or methoxy functionality. Subsequent testing of these oligosaccharides as inhibitors of mycobacterial AraT's revealed that all inhibited the enzymes, but to varying degrees. In further studies, each compound was shown to have only low activity as an inhibitor of mycobacterial growth. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.003
• 作为产物：
  描述：

  sodium methylate 、 methyl-(O⁵-methyl-2,3-anhydro-α-D-lyxofuranoside) 以 甲醇 为溶剂， 反应 72.0h， 以77%的产率得到methyl 3-O-methyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Conformational Studies of Methyl 3-O-Methyl-α-d-arabinofuranoside:  An Approach for Studying the Conformation of Furanose Rings

  摘要：

  A computational method for probing furanose conformation has been developed using a methylated monosaccharide derivative 1. First, a large library of conformers was generated by a systematic pseudo Monte Carlo search followed by optimization with the AMBER molecular mechanics force field. A subset of these conformers was then subjected to ab initio and density functional theory calculations in both the gas and aqueous phases. These calculations indicate that entropic contributions to the Gibbs free energy are important determinants of the Boltzmann distribution for the conformational preferences of 1 in the gas phase. The results obtained at each level of theory are discussed and compared with the experimentally determined conformer distribution from NMR studies in aqueous solution. In addition, the ability of each level of theory to reproduce the experimentally measured H-1-H-1 coupling constants in 1 is discussed. Empirical Karplus equations and density functional theory methods were used to determine average (3)J(H1,H2), (3)J(H2,H3), and (3) J(H3,H4) for each level of theory. On the basis of this comparison, consideration of solvation with the MN-GSM model provided good agreement with the experimental data.

  DOI：

  10.1021/ja003768s