tert-butyl 4-[(2S)-2-azido-3-[methoxy(methyl)amino]-3-oxopropyl]piperidine-1-carboxylate | 195877-51-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl 4-[(2S)-2-azido-3-[methoxy(methyl)amino]-3-oxopropyl]piperidine-1-carboxylate
• CAS: 195877-51-1
• 化学式: C₁₅H₂₇N₅O₄
• 分子量: 341.41
• InChiKey: JRIWVNMQXKGFLU-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[(2S)-2-azido-3-[methoxy(methyl)amino]-3-oxopropyl]piperidine-1-carboxylate 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Solution-phase and solid-phase synthesis of novel transition state inhibitors of coagulation enzymes incorporating a piperidinyl moiety

  摘要：

  2-Amino-3-piperidin-4-yl-propionic acid containing peptidomimetics are potent protease inhibitors when combined with an appropriate keto-thiazole or keto-carboxylic acid moiety. A novel P-1 residue in factor Xa and thrombin inhibitors has been found resulting in IC50 values as low as 0.048 mu M, a factor of ten more potent than Argatroban. Starting with non-chiral synthetic routes, a new stereospecific route was developed as well as a new solid-phase method. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00179-1
• 作为产物：
  描述：

  1-N-BOC-4-哌啶丙酸 在 lithium hydroxide 、 正丁基锂 、 2,4,6-三异丙基苯磺酰叠氮化物 、 双氧水 、 三甲基乙酰氯 、 双(三甲基硅烷基)氨基钾 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 tert-butyl 4-[(2S)-2-azido-3-[methoxy(methyl)amino]-3-oxopropyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Solution-phase and solid-phase synthesis of novel transition state inhibitors of coagulation enzymes incorporating a piperidinyl moiety

  摘要：

  2-Amino-3-piperidin-4-yl-propionic acid containing peptidomimetics are potent protease inhibitors when combined with an appropriate keto-thiazole or keto-carboxylic acid moiety. A novel P-1 residue in factor Xa and thrombin inhibitors has been found resulting in IC50 values as low as 0.048 mu M, a factor of ten more potent than Argatroban. Starting with non-chiral synthetic routes, a new stereospecific route was developed as well as a new solid-phase method. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00179-1

文献信息

• SERINE PROTEASE INHIBITORS
  申请人：Akzo Nobel N.V.

  公开号：EP1012164B1

  公开（公告）日：2004-09-22
• Solution-phase and solid-phase synthesis of novel transition state inhibitors of coagulation enzymes incorporating a piperidinyl moiety
  作者：Anton E.P. Adang、Co A.M. Peters、Siene Gerritsma、Edwin de Zwart、Gerrit Veeneman

  DOI：10.1016/s0960-894x(99)00179-1

  日期：1999.5

  2-Amino-3-piperidin-4-yl-propionic acid containing peptidomimetics are potent protease inhibitors when combined with an appropriate keto-thiazole or keto-carboxylic acid moiety. A novel P-1 residue in factor Xa and thrombin inhibitors has been found resulting in IC50 values as low as 0.048 mu M, a factor of ten more potent than Argatroban. Starting with non-chiral synthetic routes, a new stereospecific route was developed as well as a new solid-phase method. (C) 1999 Elsevier Science Ltd. All rights reserved.