(2R,3aR,6R,7S,7aS)-ethyl 6,7-bis(benzyloxy)octahydropyrano[3,2-b]pyrrole-2-carboxylate | 1041478-21-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3aR,6R,7S,7aS)-ethyl 6,7-bis(benzyloxy)octahydropyrano[3,2-b]pyrrole-2-carboxylate
• 英文别名: ethyl (2R,3aR,6R,7S,7aS)-6,7-bis(phenylmethoxy)-1,2,3,3a,5,6,7,7a-octahydropyrano[3,2-b]pyrrole-2-carboxylate
• CAS: 1041478-21-0
• 化学式: C₂₄H₂₉NO₅
• 分子量: 411.498
• InChiKey: QVOFXZWZUAEPOF-FWKCKQQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 2-amino-3-((2R,3R,4R,5R)-4,5-bis(benzyloxy)-3-(methylsulfonyloxy)tetrahydro-2H-pyran-2-yl)propanoate 在 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以50%的产率得到(2R,3aR,6R,7S,7aS)-ethyl 6,7-bis(benzyloxy)octahydropyrano[3,2-b]pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis of octahydropyrano[3,2-b]pyrrole-2-carboxylic acid derivatives from d-mannose

  摘要：

  Bicyclic amino acids are useful building blocks in synthesizing biologically active molecules and peptidomimetics. 2-Carboxy-6-hydroxyloctahydroindole (Choi) is a novel bicyclic amino acid found in the marine natural products acruginosins. Many compounds in the aeruginosin family exhibit inhibition activities toward scrine proteases including thrombin and trypsin. The unique Choi structure is the common feature of this family of oligopeptides and this motif is important for their observed biological activities. To better understand the influence of the stereochemistry of the Choi core structure on the inhibition activities, we have previously synthesized ring-oxygenated variants from glucose. The preparation of octahydro-pyrano[3,2-b]pyrrole 2-carboxylic acids from D-mannose is reported here. These novel bicyclic amino acids can be used in the preparation of aeruginosin analogs, as well as conformationally constrained peptidomimetics or other biologically active molecules. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.03.017