N-t-butoxycarbonyl-3-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)-(S)-alanine t-butyl ester | 184879-71-8

• 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: N-t-butoxycarbonyl-3-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)-(S)-alanine t-butyl ester
• 英文别名: N-t-Butoxycarbonyl-3-(1-benzyl-1,2,5,6-tetrahydro-pyridin-3-yl)-(S)-alanine t-butyl ester；tert-butyl (2S)-3-(1-benzyl-3,6-dihydro-2H-pyridin-5-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 184879-71-8
• 化学式: C₂₄H₃₆N₂O₄
• 分子量: 416.561
• InChiKey: RJABTIAEIVHZSD-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-t-butoxycarbonyl-3-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)-(S)-alanine t-butyl ester 在 甲酸 作用下， 以 水 为溶剂， 反应 22.0h， 以70%的产率得到3-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)-(S)-alanine t-butyl ester
  参考文献：
  名称：

  Synthesis of 1,2,5,6-Tetrahydro-3-pyridinylalanine: A Key Intermediate in the Preparation of Thrombin Inhibitor UK-239,326

  摘要：

  A short synthesis of N-protected 1,2,5,6-tetrahydro-3-pyridinylalanine derivatives (8-10) was accomplished using a simple procedure of quaternization of (3-pyridyl)alanine 6 with benzyl bromide followed by reduction with NaBH(4). Amino acid 10 was then converted to thrombin inhibitor UK-239,326 (2), which required the sequential functionalization of four amines to give four different functional groups (viz., sulfonamide, carboxamide, guanidine, and methylamine).

  DOI：

  10.1080/00397910701839210
• 作为产物：
  描述：

  N-t-butoxycarbonyl-3-(1-benzyl-3-pyridinium)-(S)-alanine bromide 、 N,N-二甲基甲酰胺二叔丁基缩醛 在 sodium tetrahydroborate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 5.5h， 以18.10 g的产率得到N-t-butoxycarbonyl-3-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)-(S)-alanine t-butyl ester
  参考文献：
  名称：

  Synthesis of 1,2,5,6-Tetrahydro-3-pyridinylalanine: A Key Intermediate in the Preparation of Thrombin Inhibitor UK-239,326

  摘要：

  A short synthesis of N-protected 1,2,5,6-tetrahydro-3-pyridinylalanine derivatives (8-10) was accomplished using a simple procedure of quaternization of (3-pyridyl)alanine 6 with benzyl bromide followed by reduction with NaBH(4). Amino acid 10 was then converted to thrombin inhibitor UK-239,326 (2), which required the sequential functionalization of four amines to give four different functional groups (viz., sulfonamide, carboxamide, guanidine, and methylamine).

  DOI：

  10.1080/00397910701839210

文献信息

• ANTITHROMBOTIC AMIDINOTETRAHYDROPYRIDYLALANINE DERIVATIVES
  申请人：Pfizer Research and Development Company, N.V./S.A.

  公开号：EP0822934B1

  公开（公告）日：2000-02-09
• US5798352A
  申请人：——

  公开号：US5798352A

  公开（公告）日：1998-08-25
• Synthesis of 1,2,5,6-Tetrahydro-3-pyridinylalanine: A Key Intermediate in the Preparation of Thrombin Inhibitor UK-239,326
  作者：Paul V. Fish、Alan D. Brown、John C. Danilewicz、David Ellis、J. David Hardstone、Keith James

  DOI：10.1080/00397910701839210

  日期：2008.8.19

  A short synthesis of N-protected 1,2,5,6-tetrahydro-3-pyridinylalanine derivatives (8-10) was accomplished using a simple procedure of quaternization of (3-pyridyl)alanine 6 with benzyl bromide followed by reduction with NaBH(4). Amino acid 10 was then converted to thrombin inhibitor UK-239,326 (2), which required the sequential functionalization of four amines to give four different functional groups (viz., sulfonamide, carboxamide, guanidine, and methylamine).