benzyl 6-N-acetamido-2,5-anhydro-6-deoxy-3,4-di-O-acetyl-D-gluconamide | 923267-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 6-N-acetamido-2,5-anhydro-6-deoxy-3,4-di-O-acetyl-D-gluconamide
• 英文别名: [(2R,3R,4S,5R)-2-(acetamidomethyl)-4-acetyloxy-5-(benzylcarbamoyl)oxolan-3-yl] acetate
• CAS: 923267-84-9
• 化学式: C₁₉H₂₄N₂O₇
• 分子量: 392.409
• InChiKey: PFOAHGPWRBTSFN-ZJPYXAASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 6-N-acetamido-2,5-anhydro-6-deoxy-3,4-di-O-acetyl-D-gluconamide 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以84%的产率得到(2R,3S,4S,5R)-5-(Acetylamino-methyl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid benzylamide
  参考文献：
  名称：

  Carbohydrate Amino Acids:  The Intrinsic Conformational Preference for a β-Turn-Type Structure in a Carbopeptoid Building Block

  摘要：

  Infrared ion-dip spectroscopy coupled with DFT and ab initio calculations are used to establish the intrinsic conformational preference of the basic structural unit of a peptide mimic, a cis-tetrahydrofuran-based "carbopeptoid" (amide-sugar-amide), isolated at low temperature in the gas phase. The carbopeptoid units form a beta-turn-type structure, stabilized by an intramolecular NH -> OC hydrogen bond across the sugar ring, thus forming a 10-membered, C-10 turn. Despite the clear preference for C-10 beta-turn structures in the basic unit, however, the presence of multiple hydrogen-bond donating and accepting groups also generates a rich conformational landscape, and alternative structures may be populated in related molecules. Calculations on an extended, carbopeptoid dimer unit, which includes an alternating amide-sugar-amide-sugar-amide chain, identify conformers exhibiting alternative hydrogen-bonding arrangements that are somewhat more stable than the lowest-energy double beta-turn forming conformer.

  DOI：

  10.1021/ja0607133
• 作为产物：
  描述：

  benzyl 2,5-anhydro-6-azido-6-deoxy-D-gluconamide 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 22.5h， 生成 benzyl 6-N-acetamido-2,5-anhydro-6-deoxy-3,4-di-O-acetyl-D-gluconamide
  参考文献：
  名称：

  Carbohydrate Amino Acids:  The Intrinsic Conformational Preference for a β-Turn-Type Structure in a Carbopeptoid Building Block

  摘要：

  Infrared ion-dip spectroscopy coupled with DFT and ab initio calculations are used to establish the intrinsic conformational preference of the basic structural unit of a peptide mimic, a cis-tetrahydrofuran-based "carbopeptoid" (amide-sugar-amide), isolated at low temperature in the gas phase. The carbopeptoid units form a beta-turn-type structure, stabilized by an intramolecular NH -> OC hydrogen bond across the sugar ring, thus forming a 10-membered, C-10 turn. Despite the clear preference for C-10 beta-turn structures in the basic unit, however, the presence of multiple hydrogen-bond donating and accepting groups also generates a rich conformational landscape, and alternative structures may be populated in related molecules. Calculations on an extended, carbopeptoid dimer unit, which includes an alternating amide-sugar-amide-sugar-amide chain, identify conformers exhibiting alternative hydrogen-bonding arrangements that are somewhat more stable than the lowest-energy double beta-turn forming conformer.

  DOI：

  10.1021/ja0607133