2-methyl-4,5-(3-O-(trans-3-phenylacryloyl)-4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline | 1053223-34-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-methyl-4,5-(3-O-(trans-3-phenylacryloyl)-4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline
• CAS: 1053223-34-9
• 化学式: C₂₄H₂₃NO₆
• 分子量: 421.45
• InChiKey: QNBQSKGIYYTGTJ-ROURVTSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.58
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-methyl-4,5-(3-O-(trans-3-phenylacryloyl)-4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline 在 10% Pd on charcoal 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以74%的产率得到2-acetamido-1,5-anhydro-4,6-O-benzylidene-3-O-(3-phenylpropionyl)-2-deoxy-D-glucitol
  参考文献：
  名称：

  Facile Preparation of a Highly Functionalized Tetrahydropyran by Catalytic Hydrogenation of an Oxazoline

  摘要：

  2-Amino-1,5-anhydro-2-deoxy-D-glucitol, a highly functionalized tetrahydropyran, is a versatile building unit in many natural products. A facile route to this type of synthetic building unit front the corresponding 2-aminopyranoses, as exemplified by an application to D-glucosamine, is outlined. A simple catalytic hydrogenation at C-1 of all oxazoline constructed from the corresponding 2-aminopyranose results in the desired product.

  DOI：

  10.1021/jo801037z
• 作为产物：
  描述：

  肉桂酰氯 、 2-methyl-4,5-(3-O-acetyl-4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline 在 sodium methylate 、 吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.33h， 以75%的产率得到2-methyl-4,5-(3-O-(trans-3-phenylacryloyl)-4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline
  参考文献：
  名称：

  Facile Preparation of a Highly Functionalized Tetrahydropyran by Catalytic Hydrogenation of an Oxazoline

  摘要：

  2-Amino-1,5-anhydro-2-deoxy-D-glucitol, a highly functionalized tetrahydropyran, is a versatile building unit in many natural products. A facile route to this type of synthetic building unit front the corresponding 2-aminopyranoses, as exemplified by an application to D-glucosamine, is outlined. A simple catalytic hydrogenation at C-1 of all oxazoline constructed from the corresponding 2-aminopyranose results in the desired product.

  DOI：

  10.1021/jo801037z