benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-2-pentenamido)-β-D-allopyranoside | 434948-89-7

• 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: benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-2-pentenamido)-β-D-allopyranoside
• 英文别名: (E)-N-[(2R,4aR,6R,7R,8S,8aS)-8-hydroxy-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]pent-2-enamide
• CAS: 434948-89-7
• 化学式: C₂₅H₂₉NO₆
• 分子量: 439.508
• InChiKey: HEOXLFGZRFWZOF-NHAMYJKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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-2-pentenamido)-β-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-[(2S,3R)-2,3-epoxypentanoyl]-2-N-3-O-methylidene-β-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：

  benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside 在 sodium hydroxide 、 sodium tetrahydroborate 、 三氯乙酸五氯苯酯 、 四丁基溴化铵 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 56.0h， 生成 benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-2-pentenamido)-β-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

文献信息

• Stereoselective synthesis of oxiranes using oxazolidines derived from 2-amino-2-deoxy-d-allose as chiral auxiliaries
  作者：José M. Vega-Pérez、Margarita Vega、Eugenia Blanco、Fernando Iglesias-Guerra

  DOI：10.1016/s0957-4166(01)00562-6

  日期：2001.12

  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.