1,1-Dimethylethyl N-[(1S)-1-[(chlorosulfinyl)methyl]-2-phenylethyl]carbamate | 145641-39-0

• 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: 1,1-Dimethylethyl N-[(1S)-1-[(chlorosulfinyl)methyl]-2-phenylethyl]carbamate
• 英文别名: tert-butyl N-[(2S)-1-chlorosulfinyl-3-phenylpropan-2-yl]carbamate
• CAS: 145641-39-0
• 化学式: C₁₄H₂₀ClNO₃S
• 分子量: 317.837
• InChiKey: KKNPANPBJFDOQS-SVZXGPMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-Dimethylethyl N-[(1S)-1-[(chlorosulfinyl)methyl]-2-phenylethyl]carbamate 在 N-甲基吗啉 、 ruthenium trichloride 、 sodium periodate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-phenylalanine methyl ester
  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 sodium tetrahydroborate 、 乙酸酐 、 氯 、 caesium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1,1-Dimethylethyl N-[(1S)-1-[(chlorosulfinyl)methyl]-2-phenylethyl]carbamate
  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 and evaluation of chloromethyl sulfoxides as a new class of selective irreversible cysteine protease inhibitors
  作者：Arwin J. Brouwer、Anton Bunschoten、Rob M.J. Liskamp

  DOI：10.1016/j.bmc.2007.07.045

  日期：2007.11

  The synthesis and biological evaluation of a new class of selective irreversible cysteine protease inhibitors is described. A set of amino acid based chloromethyl sulfoxides was prepared and they were found to inhibit irreversibly the cysteine protease papain. They were selective for cysteine proteases since no inhibition was found for the serine protease chymotrypsin.

  描述了新型的选择性不可逆半胱氨酸蛋白酶抑制剂的合成和生物学评估。制备了一套基于氨基酸的氯甲基亚砜，发现它们不可逆地抑制半胱氨酸蛋白酶木瓜蛋白酶。由于对丝氨酸蛋白酶胰凝乳蛋白酶没有抑制作用，因此它们对半胱氨酸蛋白酶具有选择性。
• Synthetic receptors based on peptidosulfonamide peptidomimetics
  作者：Dennis W.P.M. Löwik、Suzanne J.E. Mulders、Yuan Cheng、Yuefei Shao、Rob M.J. Liskamp

  DOI：10.1016/0040-4039(96)01882-5

  日期：1996.11

  We have synthesized tweezer-like receptor molecules based on peptidosulfonamide peptidomimetics. These compounds were screened for binding against a ∼25,000 member encoded tripeptide library. One of these synthetic receptors showed a remarkable binding selectivity.

  我们已经合成了基于肽磺酰胺拟肽的镊子样受体分子。筛选这些化合物与约25,000个成员编码的三肽文库的结合。这些合成受体之一显示出显着的结合选择性。
• Synthesis of peptides containing the β-substituted aminoethane sulfinamide or sulfonamide transition-state isostere derived from amino acids
  作者：Wilna J. Moree、Gijs A. van der Marel、Rob M.J. Liskamp

  DOI：10.1016/s0040-4039(00)60981-4

  日期：1992.10

  Alpha-amino acids can be converted to homochiral beta-substituted aminoethane sulfinamide or sulfonamide transition-state isosteres, which can be incorporated into peptides. These transition-state analogues e.g. the sulfonamide isostere of Phe-Phe will be used for the generation of catalytic antibodies as well as for the development of protease inhibitors.
• 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.