benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-α-D-allopyranoside | 434948-93-3

• 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: benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-α-D-allopyranoside
• 英文别名: (E)-N-[(2R,4aR,6S,7R,8S,8aS)-8-hydroxy-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-3-phenylprop-2-enamide
• CAS: 434948-93-3
• 化学式: C₂₉H₂₉NO₆
• 分子量: 487.552
• InChiKey: SLSGIMCKTJCKDR-RYCUPVNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-α-D-allopyranoside 在 sodium hydroxide 、 四丁基溴化铵 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-2-N-[(2R,3S)-2,3-epoxy-3-phenylpropanoyl]-2-N-3-O-methylidene-α-D-allopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of oxiranes using oxazolidines derived from 2-amino-2-deoxy-d-allose as chiral auxiliaries

  摘要：

  The synthesis of 2,3-epoxyamide derivatives of 2-amino-2-deoxy-D-allose is described. Epoxidation of the corresponding alpha,beta-unsaturated amides with m-CPBA took place with better stereoselectivity when an oxazolidine ring was fused to the 2,3-positions of the sugar molecule. In most cases, both stereoisomers could be isolated and characterized. The stereochemistry of the new stereogenic centers was then determined by cleavage of the,oxirane moiety from the chiral auxiliary, which was also recovered. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00562-6
• 作为产物：
  描述：

  3-苯基-2-丙烯酰氯 、 benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-α-D-allopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of oxiranes using oxazolidines derived from 2-amino-2-deoxy-d-allose as chiral auxiliaries

  摘要：

  The synthesis of 2,3-epoxyamide derivatives of 2-amino-2-deoxy-D-allose is described. Epoxidation of the corresponding alpha,beta-unsaturated amides with m-CPBA took place with better stereoselectivity when an oxazolidine ring was fused to the 2,3-positions of the sugar molecule. In most cases, both stereoisomers could be isolated and characterized. The stereochemistry of the new stereogenic centers was then determined by cleavage of the,oxirane moiety from the chiral auxiliary, which was also recovered. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00562-6