(RS)-2-<(tert-Butoxycarbonyl)amino>-1-phenylpropyl thioacetate | 167867-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (RS)-2-<(tert-Butoxycarbonyl)amino>-1-phenylpropyl thioacetate
• 英文别名: S-[1-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropan-2-yl] ethanethioate
• CAS: 167867-21-2
• 化学式: C₁₆H₂₃NO₃S
• 分子量: 309.43
• InChiKey: XLKABMYJHLCGGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (RS)-2-<(tert-Butoxycarbonyl)amino>-1-phenylpropyl thioacetate 在 磺酰氯 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(tert-Butoxycarbonyl)-1(RS)-benzylhypotauryl chloride
  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：

  2-羟基3-苯基丙腈 在 N-甲基吗啉 、 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (RS)-2-<(tert-Butoxycarbonyl)amino>-1-phenylpropyl thioacetate
  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.