allyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside | 161687-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside
• 英文别名: [(4aR,6S,7R,8S,8aR)-7-benzoyloxy-2-phenyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
• CAS: 161687-18-9
• 化学式: C₃₀H₂₈O₈
• 分子量: 516.548
• InChiKey: XQYBZAHYBXZEQF-LUQCHYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 4 A molecular sieve 、 三乙基硅基三氟甲磺酸酯 、 一水合肼 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Synthesis of sulfur analogues of methyl and allyl kojibiosides and methyl isomaltoside and conformational analysis of the kojibiosides

  摘要：

  The synthesis of methyl and allyl 5'-thio-alpha-D-kojibiosides and methyl 5'-thio-alpha-D-isomaltoside is described. The phenylselenoglycoside and trichloroacetimidate of 2,3,4,6-tetra-O-acetyl-5-thioglucose have been employed as glycosyl donors to glycosylate glucopyranosyl accepters with 2-OH and 6-OH positions free. The disaccharides thus obtained are potential glucosidase inhibitors. The conformational preferences of allyl 5'-thiokojibioside (34) were studied by comparison of experimental NOE curves with the theoretical counterparts for the corresponding methyl glycoside 25, derived from a Boltzmann-averaged grid search using the program PIMM91. Very goad agreement of experimental NOE curves derived from selective NOE measurements with the theoretical curves is found. The data are consistent with the population of a global minimum structure Phi=-43, Psi-39 degrees) to the extent of 90%, and a second local minimum (Phi=-36, Psi=-173 degrees) to the extent of 6%. An X-ray crystal structure of 34 at 190 K (R=4.2%) indicates a conformation (Phi=-46, Psi=-23 degrees) that is similar to that of the global minimum.

  DOI：

  10.1016/s0957-4166(00)80386-9
• 作为产物：
  描述：

  allyl D-glucopyranoside 在 吡啶 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 allyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of sulfur analogues of methyl and allyl kojibiosides and methyl isomaltoside and conformational analysis of the kojibiosides

  摘要：

  The synthesis of methyl and allyl 5'-thio-alpha-D-kojibiosides and methyl 5'-thio-alpha-D-isomaltoside is described. The phenylselenoglycoside and trichloroacetimidate of 2,3,4,6-tetra-O-acetyl-5-thioglucose have been employed as glycosyl donors to glycosylate glucopyranosyl accepters with 2-OH and 6-OH positions free. The disaccharides thus obtained are potential glucosidase inhibitors. The conformational preferences of allyl 5'-thiokojibioside (34) were studied by comparison of experimental NOE curves with the theoretical counterparts for the corresponding methyl glycoside 25, derived from a Boltzmann-averaged grid search using the program PIMM91. Very goad agreement of experimental NOE curves derived from selective NOE measurements with the theoretical curves is found. The data are consistent with the population of a global minimum structure Phi=-43, Psi-39 degrees) to the extent of 90%, and a second local minimum (Phi=-36, Psi=-173 degrees) to the extent of 6%. An X-ray crystal structure of 34 at 190 K (R=4.2%) indicates a conformation (Phi=-46, Psi=-23 degrees) that is similar to that of the global minimum.

  DOI：

  10.1016/s0957-4166(00)80386-9

文献信息

• Synthesis of sulfur analogues of methyl and allyl kojibiosides and methyl isomaltoside and conformational analysis of the kojibiosides
  作者：Seema Mehta、Kelly L. Jordan、Thomas Weimar、Uwe C. Kreis、Raymond J. Batchelor、Frederick W.B. Einstein、B.Mario Pinto

  DOI：10.1016/s0957-4166(00)80386-9

  日期：1994.12

  The synthesis of methyl and allyl 5'-thio-alpha-D-kojibiosides and methyl 5'-thio-alpha-D-isomaltoside is described. The phenylselenoglycoside and trichloroacetimidate of 2,3,4,6-tetra-O-acetyl-5-thioglucose have been employed as glycosyl donors to glycosylate glucopyranosyl accepters with 2-OH and 6-OH positions free. The disaccharides thus obtained are potential glucosidase inhibitors. The conformational preferences of allyl 5'-thiokojibioside (34) were studied by comparison of experimental NOE curves with the theoretical counterparts for the corresponding methyl glycoside 25, derived from a Boltzmann-averaged grid search using the program PIMM91. Very goad agreement of experimental NOE curves derived from selective NOE measurements with the theoretical curves is found. The data are consistent with the population of a global minimum structure Phi=-43, Psi-39 degrees) to the extent of 90%, and a second local minimum (Phi=-36, Psi=-173 degrees) to the extent of 6%. An X-ray crystal structure of 34 at 190 K (R=4.2%) indicates a conformation (Phi=-46, Psi=-23 degrees) that is similar to that of the global minimum.