(3R,4S)-1-benzyloxycarbonyl-3-tert-butoxycarbonylamino-4-hydroxypyrrolidine

• 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: (3R,4S)-1-benzyloxycarbonyl-3-tert-butoxycarbonylamino-4-hydroxypyrrolidine
• 英文别名: Benzyl (3R,4S)-3-((tert-butoxycarbonyl)amino)-4-hydroxypyrrolidine-1-carboxylate；benzyl (3S,4R)-3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-1-carboxylate
• 化学式: C₁₇H₂₄N₂O₅
• 分子量: 336.388
• InChiKey: CMXBVXJSFDXHTE-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S)-1-benzyloxycarbonyl-3-tert-butoxycarbonylamino-4-hydroxypyrrolidine 在 盐酸 、 immobilized Candida antarctica lipase A 、 水 、 potassium carbonate 作用下， 以 乙醇 、 甲基叔丁基醚 、 乙腈 为溶剂， 反应 62.0h， 生成 (3S,4R)-(+)-1-benzyloxycarbonyl-3-amino-4-hydroxypyrrolidine
  参考文献：
  名称：

  Enzymatic preparation of cis and trans-3-amino-4-hydroxytetrahydrofurans and cis-3-amino-4-hydroxypyrrolidines

  摘要：

  The lipase catalyzed resolution of cis and trans-3-amino-4-hydroxytetrahydraurans and cis-3-amino-4-hydroxypyrrolidines have been studied. For all the heterocycles, the best enantioselectivity was obtained using Candida antarctica lipases A and B as catalysts in hydrolytic processes. The absolute configuration of the optically pure obtained heterocycles has been assigned. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.05.014
• 作为产物：
  描述：

  3-吡咯烷-1-甲酸苄酯 在 咪唑 、 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 水 、 sodium hydroxide 、 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 (3R,4S)-1-benzyloxycarbonyl-3-tert-butoxycarbonylamino-4-hydroxypyrrolidine
  参考文献：
  名称：

  Enzymatic preparation of cis and trans-3-amino-4-hydroxytetrahydrofurans and cis-3-amino-4-hydroxypyrrolidines

  摘要：

  The lipase catalyzed resolution of cis and trans-3-amino-4-hydroxytetrahydraurans and cis-3-amino-4-hydroxypyrrolidines have been studied. For all the heterocycles, the best enantioselectivity was obtained using Candida antarctica lipases A and B as catalysts in hydrolytic processes. The absolute configuration of the optically pure obtained heterocycles has been assigned. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.05.014

文献信息

• Enzymatic preparation of cis and trans-3-amino-4-hydroxytetrahydrofurans and cis-3-amino-4-hydroxypyrrolidines
  作者：Ángela Villar-Barro、Vicente Gotor、Rosario Brieva

  DOI：10.1016/j.bmc.2014.05.014

  日期：2014.10

  The lipase catalyzed resolution of cis and trans-3-amino-4-hydroxytetrahydraurans and cis-3-amino-4-hydroxypyrrolidines have been studied. For all the heterocycles, the best enantioselectivity was obtained using Candida antarctica lipases A and B as catalysts in hydrolytic processes. The absolute configuration of the optically pure obtained heterocycles has been assigned. (C) 2014 Elsevier Ltd. All rights reserved.