pent-4-enyl 6-O-benzyl-2,3-O-ethylene-β-D-glucopyranoside | 178249-60-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: pent-4-enyl 6-O-benzyl-2,3-O-ethylene-β-D-glucopyranoside
• 英文别名: (4aR,5R,7R,8R,8aS)-5-pent-4-enoxy-7-(phenylmethoxymethyl)-3,4a,5,7,8,8a-hexahydro-2H-pyrano[3,4-b][1,4]dioxin-8-ol
• CAS: 178249-60-0
• 化学式: C₂₀H₂₈O₆
• 分子量: 364.439
• InChiKey: YTUZMORVUKCLMV-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 pent-4-enyl 6-O-benzyl-2,3-O-ethylene-β-D-glucopyranoside 在 sodium hydride 作用下， 生成 pent-4-enyl 4,6-di-O-benzyl-2,3-O-ethylene-β-D-glucopyranoside
  参考文献：
  名称：

  A Solvation-Assisted Model for Estimating Anomeric Reactivity. Predicted versus Observed Trends in Hydrolysis of n-Pentenyl Glycosides¹

  摘要：

  An attempt has been made to predict qualitative trends in reactivity at the anomeric center, using N-bromosuccinimide-induced hydrolysis of n-pentenyl glycosides (NPGs) as the experimental model. Calculated relative activation energies based on internal energy differences between a reactant and the associated intermediate are not always in agreement with experimental observations. However, solvation energies obtained by the generalized Born surface area model in MacroModel developed by Still et al. give modified activation energies that are in excellent agreement with the experimentally observed trends. It is shown that the solvation model does not disturb the normally observed reactivity trends that can be rationalized on the basis of internal energies alone. The value of the methodology has been demonstrated for several substrates by first-calculating their relative activation energies, then testing them experimentally, and finding excellent agreement with predictions.

  DOI：

  10.1021/jo9601223
• 作为产物：
  描述：

  pent-4-enyl 4,6-O-benzylidene-2,3-O-ethylene-β-D-glucopyranoside 在 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到pent-4-enyl 6-O-benzyl-2,3-O-ethylene-β-D-glucopyranoside
  参考文献：
  名称：

  A Solvation-Assisted Model for Estimating Anomeric Reactivity. Predicted versus Observed Trends in Hydrolysis of n-Pentenyl Glycosides¹

  摘要：

  An attempt has been made to predict qualitative trends in reactivity at the anomeric center, using N-bromosuccinimide-induced hydrolysis of n-pentenyl glycosides (NPGs) as the experimental model. Calculated relative activation energies based on internal energy differences between a reactant and the associated intermediate are not always in agreement with experimental observations. However, solvation energies obtained by the generalized Born surface area model in MacroModel developed by Still et al. give modified activation energies that are in excellent agreement with the experimentally observed trends. It is shown that the solvation model does not disturb the normally observed reactivity trends that can be rationalized on the basis of internal energies alone. The value of the methodology has been demonstrated for several substrates by first-calculating their relative activation energies, then testing them experimentally, and finding excellent agreement with predictions.

  DOI：

  10.1021/jo9601223