2-((2-methyl-2-propyl)thio)-1-phenylethyl phenyl carbonate | 147529-17-7

• 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: 2-((2-methyl-2-propyl)thio)-1-phenylethyl phenyl carbonate
• 英文别名: (2-Tert-butylsulfanyl-1-phenylethyl) phenyl carbonate
• CAS: 147529-17-7
• 化学式: C₁₉H₂₂O₃S
• 分子量: 330.448
• InChiKey: MKBGSCRKHBMJAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((2-methyl-2-propyl)thio)-1-phenylethyl phenyl carbonate 在 苄基三甲基氢氧化铵 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 N-<<2-<2-nitrophenyl)dithio>-1-phenylethoxy>carbonyl>glycylglycine benzyl ester
  参考文献：
  名称：

  An affinity chromatographic method for the purification of water-insoluble peptides

  摘要：

  A simple and efficient affinity chromatographic method is described for the purification of hydrophobic and/or protected synthetic peptides in organic solvent. This affinity method entails the use of a new protecting group that contains a UV-active disulfide moiety ([2-[(2-nitrophenyl)dithio]-1-phenylethoxy]carbonyl, NpSSPeoc). NpSSPeoc is electrophilic and can be immobilized by a thiolate-disulfide interchange reaction on a thiol-containing solid support. Alternatively, NpSSPeoc can be converted into a nucleophilic thiol ((2-mercapto-1-phenylethoxy)carbonyl, HSPeoc) and immobilized by an electrophilic solid support. NpSSPeoc can be quantified via an Ellman-type assay to measure the amount of full-length peptide at the completion of a solid-phase synthesis before and/or after cleavage from the synthesis resin. NpSSPeoc can be removed with 25% trifluoroacetic acid in methylene chloride. Four peptides incorporating NpSSPeoc at the N-terminus were synthesized. Affinity chromatography was performed on these peptides using 1 % cross-linked polystyrene supports which incorporate a mercury(II) trifluoroacetate, disulfide, alkyl thiol, or iodoacetamide functionality. The results indicate that the highest and most consistent yields of purified peptide are obtained using the combination of HSPeoc and a polystyrene support incorporating the iodoacetamide functionality.

  DOI：

  10.1021/jo00058a007
• 作为产物：
  描述：

  α-(tert-Butylthio)acetophenone 在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 49.58h， 生成 2-((2-methyl-2-propyl)thio)-1-phenylethyl phenyl carbonate
  参考文献：
  名称：

  An affinity chromatographic method for the purification of water-insoluble peptides

  摘要：

  A simple and efficient affinity chromatographic method is described for the purification of hydrophobic and/or protected synthetic peptides in organic solvent. This affinity method entails the use of a new protecting group that contains a UV-active disulfide moiety ([2-[(2-nitrophenyl)dithio]-1-phenylethoxy]carbonyl, NpSSPeoc). NpSSPeoc is electrophilic and can be immobilized by a thiolate-disulfide interchange reaction on a thiol-containing solid support. Alternatively, NpSSPeoc can be converted into a nucleophilic thiol ((2-mercapto-1-phenylethoxy)carbonyl, HSPeoc) and immobilized by an electrophilic solid support. NpSSPeoc can be quantified via an Ellman-type assay to measure the amount of full-length peptide at the completion of a solid-phase synthesis before and/or after cleavage from the synthesis resin. NpSSPeoc can be removed with 25% trifluoroacetic acid in methylene chloride. Four peptides incorporating NpSSPeoc at the N-terminus were synthesized. Affinity chromatography was performed on these peptides using 1 % cross-linked polystyrene supports which incorporate a mercury(II) trifluoroacetate, disulfide, alkyl thiol, or iodoacetamide functionality. The results indicate that the highest and most consistent yields of purified peptide are obtained using the combination of HSPeoc and a polystyrene support incorporating the iodoacetamide functionality.

  DOI：

  10.1021/jo00058a007

文献信息

• An affinity chromatographic method for the purification of water-insoluble peptides
  作者：Irving Sucholeiki、Peter T. Lansbury

  DOI：10.1021/jo00058a007

  日期：1993.3

  A simple and efficient affinity chromatographic method is described for the purification of hydrophobic and/or protected synthetic peptides in organic solvent. This affinity method entails the use of a new protecting group that contains a UV-active disulfide moiety ([2-[(2-nitrophenyl)dithio]-1-phenylethoxy]carbonyl, NpSSPeoc). NpSSPeoc is electrophilic and can be immobilized by a thiolate-disulfide interchange reaction on a thiol-containing solid support. Alternatively, NpSSPeoc can be converted into a nucleophilic thiol ((2-mercapto-1-phenylethoxy)carbonyl, HSPeoc) and immobilized by an electrophilic solid support. NpSSPeoc can be quantified via an Ellman-type assay to measure the amount of full-length peptide at the completion of a solid-phase synthesis before and/or after cleavage from the synthesis resin. NpSSPeoc can be removed with 25% trifluoroacetic acid in methylene chloride. Four peptides incorporating NpSSPeoc at the N-terminus were synthesized. Affinity chromatography was performed on these peptides using 1 % cross-linked polystyrene supports which incorporate a mercury(II) trifluoroacetate, disulfide, alkyl thiol, or iodoacetamide functionality. The results indicate that the highest and most consistent yields of purified peptide are obtained using the combination of HSPeoc and a polystyrene support incorporating the iodoacetamide functionality.