methyl-(O⁵-methyl-2,3-anhydro-α-D-lyxofuranoside) | 911481-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: methyl-(O⁵-methyl-2,3-anhydro-α-D-lyxofuranoside)
• 英文别名: Methyl-(O⁵-methyl-2,3-anhydro-α-D-lyxofuranosid)；(1S,2S,4R,5S)-2-methoxy-4-(methoxymethyl)-3,6-dioxabicyclo[3.1.0]hexane
• CAS: 911481-40-8
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: LHXBJXXHEMDHNU-BWBBJGPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl-(O⁵-methyl-2,3-anhydro-α-D-lyxofuranoside) 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 methyl 3-O-allyl-2,5-di-O-benzyl-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
• 作为产物：
  描述：

  methyl 2,3-anhydro-α-D-lyxofuranoside 、 碘甲烷 在 silver(l) oxide 作用下， 生成 methyl-(O⁵-methyl-2,3-anhydro-α-D-lyxofuranoside)
  参考文献：
  名称：

  113.由2-甲苯-对-磺酰基甲基-D-木呋喃糖苷制备2：3-脱水甲基-D-糖苷，并合成2-甲基D-木糖，3-甲基D-阿拉伯糖和3：5-二甲基D-阿拉伯糖

  摘要：

  DOI：

  10.1039/jr9530000564

文献信息

• 175. The ammonolysis of methyl 2 : 3-anhydro-<scp>D</scp>-furanosides. Part II. Methyl 2 : 3-anhydro-5-O-methyl-α- and -β-<scp>D</scp>-lyxofuranosides
  作者：J. M. Anderson、Elizabeth Percival

  DOI：10.1039/jr9560000819

  日期：——
• 113. The preparation of 2 : 3-anhydromethyl-D-lyxoside from 2-toluene-p-sulphonyl methyl-D-xylofuranoside, and synthesis of 2-methyl D-xylose, 3-methyl D-arabinose, and 3 : 5-dimethyl D-arabinose
  作者：E. E. Percival、Rolf Zobrist

  DOI：10.1039/jr9530000564

  日期：——
• Conformational Studies of Methyl 3-<i>O</i>-Methyl-α-<scp>d</scp>-arabinofuranoside:  An Approach for Studying the Conformation of Furanose Rings
  作者：Justin B. Houseknecht、Patrick R. McCarren、Todd L. Lowary、Christopher M. Hadad

  DOI：10.1021/ja003768s

  日期：2001.9.1

  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.