N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide | 167867-38-1

• 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: N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide
• 英文别名: tert-butyl N-[(2S)-1-[[(2S)-1-[[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]sulfonyl]-3-phenylpropan-2-yl]amino]-4-amino-1,4-dioxobutan-2-yl]carbamate
• CAS: 167867-38-1
• 化学式: C₃₂H₅₁N₅O₇S
• 分子量: 649.852
• InChiKey: KVGVZASDPPIXQI-UUNMLIRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  185
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到(2S)-N-[(2S)-1-[[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]sulfonyl]-3-phenylpropan-2-yl]-2-aminobutanediamide
  参考文献：
  名称：

  Synthesis of Peptidosulfinamides and Peptidosulfonamides: Peptidomimetics Containing the Sulfinamide or Sulfonamide Transition-State Isostere

  摘要：

  Synthetic routes are described toward the preparation of alpha- as well as beta-substituted aminoethanesulfinyl chlorides, starting from either an aldehyde or from an amino acid derivative. The sulfinyl chlorides are used as building blocks for the preparation of homochiral alpha- or beta- substituted sulfinamide and sulfonamide transition-state isosteres. The methodology has been applied to the synthesis of peptidosulfonamide peptidomimetics such as a hapten needed for the generation of antibodies and potential HIV protease inhibitors. In addition, the beta-substituted aminoethanesulfinyl chlorides were used as building blocks for the preparation of a tetrapeptidosulfonamide, which can be considered as a biopolymer mimetic, employing a repetition of a cycle of three reactions: coupling of the sulfinyl chloride to the N-terminus of the growing peptidosulfonamide, oxidation to the sulfonamide, and deprotection of the N-terminus.

  DOI：

  10.1021/jo00121a038
• 作为产物：
  描述：

  ethoxycarbonyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate 在 N-甲基吗啉 、 ruthenium trichloride 、 sodium tetrahydroborate 、 sodium periodate 、 乙酸酐 、 氯 、 1-羟基苯并三唑 、 caesium carbonate 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide
  参考文献：
  名称：

  Synthesis of Peptidosulfinamides and Peptidosulfonamides: Peptidomimetics Containing the Sulfinamide or Sulfonamide Transition-State Isostere

  摘要：

  Synthetic routes are described toward the preparation of alpha- as well as beta-substituted aminoethanesulfinyl chlorides, starting from either an aldehyde or from an amino acid derivative. The sulfinyl chlorides are used as building blocks for the preparation of homochiral alpha- or beta- substituted sulfinamide and sulfonamide transition-state isosteres. The methodology has been applied to the synthesis of peptidosulfonamide peptidomimetics such as a hapten needed for the generation of antibodies and potential HIV protease inhibitors. In addition, the beta-substituted aminoethanesulfinyl chlorides were used as building blocks for the preparation of a tetrapeptidosulfonamide, which can be considered as a biopolymer mimetic, employing a repetition of a cycle of three reactions: coupling of the sulfinyl chloride to the N-terminus of the growing peptidosulfonamide, oxidation to the sulfonamide, and deprotection of the N-terminus.

  DOI：

  10.1021/jo00121a038

文献信息

• Synthesis of Peptidosulfinamides and Peptidosulfonamides: Peptidomimetics Containing the Sulfinamide or Sulfonamide Transition-State Isostere
  作者：Wilna J. Moree、Gijs A. van der Marel、Rob J. Liskamp

  DOI：10.1021/jo00121a038

  日期：1995.8

  Synthetic routes are described toward the preparation of alpha- as well as beta-substituted aminoethanesulfinyl chlorides, starting from either an aldehyde or from an amino acid derivative. The sulfinyl chlorides are used as building blocks for the preparation of homochiral alpha- or beta- substituted sulfinamide and sulfonamide transition-state isosteres. The methodology has been applied to the synthesis of peptidosulfonamide peptidomimetics such as a hapten needed for the generation of antibodies and potential HIV protease inhibitors. In addition, the beta-substituted aminoethanesulfinyl chlorides were used as building blocks for the preparation of a tetrapeptidosulfonamide, which can be considered as a biopolymer mimetic, employing a repetition of a cycle of three reactions: coupling of the sulfinyl chloride to the N-terminus of the growing peptidosulfonamide, oxidation to the sulfonamide, and deprotection of the N-terminus.