4-methyl-1-{N-[1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-[1-(N,N'-di-t-butoxycarbonylamidino)-1,2,5,6-tetrahydro-3-pyridyl]-(S)-alanyl}-1,2,3,6-tetrahydropyridine-2(R)-carboxylic acid methyl ester | 184879-80-9

• 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: 4-methyl-1-{N-[1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-[1-(N,N'-di-t-butoxycarbonylamidino)-1,2,5,6-tetrahydro-3-pyridyl]-(S)-alanyl}-1,2,3,6-tetrahydropyridine-2(R)-carboxylic acid methyl ester
• 英文别名: methyl (2R)-1-[(2S)-3-[1-[(Z)-N,N'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-3,6-dihydro-2H-pyridin-5-yl]-2-(1,2,3,4-tetrahydroisoquinolin-7-ylsulfonylamino)propanoyl]-4-methyl-3,6-dihydro-2H-pyridine-2-carboxylate
• CAS: 184879-80-9
• 化学式: C₃₆H₅₂N₆O₉S
• 分子量: 744.91
• InChiKey: ZERNFYZUOMIHPQ-URLMMPGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  52
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  193
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 4-methyl-1-{N-[1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-[1-(N,N'-di-t-butoxycarbonylamidino)-1,2,5,6-tetrahydro-3-pyridyl]-(S)-alanyl}-1,2,3,6-tetrahydropyridine-2(R)-carboxylic acid methyl ester 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.5h， 以66%的产率得到4-methyl-1-{N-[2-methyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-[1-(N,N'-di-t-butoxycarbonylamidino)-1,2,5,6-tetrahydro-3-pyridyl]-(S)-alanyl}-1,2,3,6-tetrahydropyridine-2(R)-carboxylic acid methyl 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：

  4-methyl-1-{N-[2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-[1-(N,N'-di-t-butoxycarbonylamidino)-1,2,5,6-tetrahydro-3-pyridyl]-(S)-alanyl}-1,2,3,6-tetrahydropyridine-2(R)-carboxylic acid methyl ester 在 水 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以85%的产率得到4-methyl-1-{N-[1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-[1-(N,N'-di-t-butoxycarbonylamidino)-1,2,5,6-tetrahydro-3-pyridyl]-(S)-alanyl}-1,2,3,6-tetrahydropyridine-2(R)-carboxylic acid methyl 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
• 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).