(S)-benzyl 2-(((3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamido)methyl)pyrrolidine-1-carboxylate | 1599474-01-7

• 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: (S)-benzyl 2-(((3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamido)methyl)pyrrolidine-1-carboxylate
• CAS: 1599474-01-7
• 化学式: C₂₈H₃₄N₂O₇
• 分子量: 510.587
• InChiKey: PMUKEIXQKOSZDT-IIDPJMFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.56
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 2-(((3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamido)methyl)pyrrolidine-1-carboxylate 在 氢气 、 钯 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以82%的产率得到(3aR,5S,6R,6aR)-6-hydroxy-2,2-dimethyl-N-((S)-pyrrolidin-2-ylmethyl)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamide
  参考文献：
  名称：

  Sugar amide-pyrrolidine catalyst for the asymmetric Michael addition of ketones to nitroolefins

  摘要：

  New sugar amide-pyrrolidine derivatives possessing the furano form of the carbohydrate template were designed and developed as efficient and stereoselective organocatalysts for asymmetric Michael additions of ketones to nitroolefins at room temperature. Good yields and high selectivities were achieved with catalyst 2 under solvent-free and additive-free reaction conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.02.003
• 作为产物：
  描述：

  1, 2-O-(1-methylethylidene)-3-O-(phenylmethyl)-α-D-xylofuranuronic acid 、 (S)-2-氨甲基-1-M-Cbz-吡咯烷 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.25h， 以77%的产率得到(S)-benzyl 2-(((3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamido)methyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Sugar amide-pyrrolidine catalyst for the asymmetric Michael addition of ketones to nitroolefins

  摘要：

  New sugar amide-pyrrolidine derivatives possessing the furano form of the carbohydrate template were designed and developed as efficient and stereoselective organocatalysts for asymmetric Michael additions of ketones to nitroolefins at room temperature. Good yields and high selectivities were achieved with catalyst 2 under solvent-free and additive-free reaction conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.02.003