pent-4-enyl α-D-glucopyranoside | 125647-51-0

• 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 α-D-glucopyranoside
• 英文别名: pentenyl glucoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-pent-4-enoxyoxane-3,4,5-triol
• CAS: 125647-51-0
• 化学式: C₁₁H₂₀O₆
• 分子量: 248.276
• InChiKey: NIFLCEUASFWSRL-NZFPMDFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  pent-4-enyl α-D-glucopyranoside 在 sodium hydroxide 、 四丁基溴化铵 、 4-甲基苯磺酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 51.5h， 生成 pent-4-enyl 4,6-O-benzylidene-2,3-O-ethylene-α-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 D-glucopyranoside 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 pent-4-enyl α-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

文献信息

• Protection-free Synthesis of Alkyl Glycosides under Hydrogenolytic Conditions
  作者：Masaki Ishihara、Yuka Takagi、Gefei Li、Masato Noguchi、Shin-ichiro Shoda

  DOI：10.1246/cl.130646

  日期：2013.10.5

  A convenient protection-free synthetic route for the preparation of alkyl glycosides has been developed. The alcoholysis of one-step preparable glycosyl donors, 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) glycosides, under hydrogenolytic conditions gave the corresponding glycosides in good yields without the addition of any acid promoters. The method could be successfully applied to the glycosylation of an acid-labile oligosaccharide.

  已开发出一种方便的无保护合成路线用于烷基糖苷的制备。在氢解条件下，一步可制备的糖苷供体4,6-二苯氧基-1,3,5-三嗪-2-基(DBT)糖苷的醇解反应，能够在不添加任何酸催化剂的情况下，以良好的产率得到相应的糖苷。该方法可以成功应用于酸不稳定的寡糖的糖基化。
• Efficient glycosylation of unprotected sugars using sulfamic acid: A mild eco-friendly catalyst
  作者：Goutam Guchhait、Anup Kumar Misra

  DOI：10.1016/j.catcom.2011.07.016

  日期：2011.10

  Sulfamic acid, a mild and environmentally benign catalyst has been successfully used in the Fischer glycosylation of unprotected sugars for the preparation alkyl glycosides. A diverse range of aliphatic alcohols have been used to prepare a series of alkyl glycosides in good to excellent yield. (C) 2011 Elsevier B.V. All rights reserved.
• Konstantinović; Predojević; Gojković, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 3, p. 666 - 669
  作者：Konstantinović、Predojević、Gojković、Pavlović

  DOI：——

  日期：——
• RATCLIFFE, ANDREW J.;FRASER-REID, BERT, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N0, C. 1805-1810
  作者：RATCLIFFE, ANDREW J.、FRASER-REID, BERT

  DOI：——

  日期：——
• A Solvation-Assisted Model for Estimating Anomeric Reactivity. Predicted versus Observed Trends in Hydrolysis of <i>n</i>-Pentenyl Glycosides¹
  作者：C. Webster Andrews、Robert Rodebaugh、Bert Fraser-Reid

  DOI：10.1021/jo9601223

  日期：1996.1.1

  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.