tert-butyl (3R,4R)-3-[[4-methyl-6-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-enylamino]pyridin-2-yl]methyl]-4-[(2-methylpropan-2-yl)oxycarbonyloxy]pyrrolidine-1-carboxylate | 1221064-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (3R,4R)-3-[[4-methyl-6-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-enylamino]pyridin-2-yl]methyl]-4-[(2-methylpropan-2-yl)oxycarbonyloxy]pyrrolidine-1-carboxylate
• CAS: 1221064-99-8
• 化学式: C₂₉H₄₅N₃O₇
• 分子量: 547.692
• InChiKey: BYDFFTMQFXKKEC-IRLDBZIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (3R,4R)-3-[[4-methyl-6-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-enylamino]pyridin-2-yl]methyl]-4-[(2-methylpropan-2-yl)oxycarbonyloxy]pyrrolidine-1-carboxylate 在 水 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以1.05 g的产率得到(3R,4R)-tert-butyl 3-((6-(allyl(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate
  参考文献：
  名称：

  An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application

  摘要：

  We report a fast N -> O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.009
• 作为产物：
  描述：

  (3R,4R)-tert-butyl 3-((6-(tert-butoxycarbonylamino)-4-methylpyridin-2-yl)methyl)-4-(tert-butoxycarbonyloxy)pyrrolidine-1-carboxylate 、 3-溴丙烯 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 以525 mg的产率得到tert-butyl (3R,4R)-3-[[4-methyl-6-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-enylamino]pyridin-2-yl]methyl]-4-[(2-methylpropan-2-yl)oxycarbonyloxy]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application

  摘要：

  We report a fast N -> O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.009

文献信息

• An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application
  作者：Fengtian Xue、Richard B. Silverman

  DOI：10.1016/j.tetlet.2010.03.009

  日期：2010.5

  We report a fast N -> O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state. (C) 2010 Elsevier Ltd. All rights reserved.