N,O-Ditosyl-L-threonine methyl ester | 134019-97-9

• 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: N,O-Ditosyl-L-threonine methyl ester
• 英文别名: N,O-Ditosyl-L-threoninmethylester；(Tos)2-D-threo-Thr-OCH3；(Tos)2-L-threo-Thr-OCH3；methyl (2S,3R)-2-[(4-methylphenyl)sulfonylamino]-3-(4-methylphenyl)sulfonyloxybutanoate
• CAS: 134019-97-9
• 化学式: C₁₉H₂₃NO₇S₂
• 分子量: 441.526
• InChiKey: RNBFSFJYVMVOMS-QAPCUYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,O-Ditosyl-L-threonine methyl ester 在 sodium tetrahydroborate 、 戴斯-马丁氧化剂 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl (E)-3-[(2R,3S)-3-methyl-1-(4-methylphenyl)sulfonylaziridin-2-yl]prop-2-enoate
  参考文献：
  名称：

  SN2'-Reactions of Peptide Aziridines. A Cuprate-Based Approach to (E)-Alkene Isosteres

  摘要：

  Alkenylaziridines were prepared from allylic alcohols via Sharpless epoxidation; oxirane to aziridine conversion under modified Staudinger conditions, and Wittig chain extension. Alternatively, beta-hydroxy alpha-amino acids such as threonine can serve as readily available precursors. The corresponding N-acyl, -peptidyl-, -carbamoyl-, and -sulfonylaziridines underwent a high-yielding anti-S(N)2' alkylation with organocopper/BF3 complex to give (E)-alkene peptide isosteres in 62 to >98% de. The stereoselectivity of the addition process was studied by H-1 and F-19 NMR as well as chemical degradation. Alkene isosteres are important nonhydrolyzable and rigidified analogs of peptide bonds in biologically active peptides. This new methodology considerably facilitates the synthesis and the study of these peptide mimetics, since alkenylaziridines are readily prepared and side-chain modification is simplified by the wide range of functionalized organocopper reagents that are available.

  DOI：

  10.1021/jo00096a033
• 作为产物：
  描述：

  L-苏氨酸甲酯盐酸盐 、 对甲苯磺酰氯 以 吡啶 为溶剂， 以37%的产率得到N,O-Ditosyl-L-threonine methyl ester
  参考文献：
  名称：

  SN2'-Reactions of Peptide Aziridines. A Cuprate-Based Approach to (E)-Alkene Isosteres

  摘要：

  Alkenylaziridines were prepared from allylic alcohols via Sharpless epoxidation; oxirane to aziridine conversion under modified Staudinger conditions, and Wittig chain extension. Alternatively, beta-hydroxy alpha-amino acids such as threonine can serve as readily available precursors. The corresponding N-acyl, -peptidyl-, -carbamoyl-, and -sulfonylaziridines underwent a high-yielding anti-S(N)2' alkylation with organocopper/BF3 complex to give (E)-alkene peptide isosteres in 62 to >98% de. The stereoselectivity of the addition process was studied by H-1 and F-19 NMR as well as chemical degradation. Alkene isosteres are important nonhydrolyzable and rigidified analogs of peptide bonds in biologically active peptides. This new methodology considerably facilitates the synthesis and the study of these peptide mimetics, since alkenylaziridines are readily prepared and side-chain modification is simplified by the wide range of functionalized organocopper reagents that are available.

  DOI：

  10.1021/jo00096a033

文献信息

• Syntheses of actinomycin and analogs. VIII. Synthesis of actinomycin D lactam
  作者：Eric Atherton、Johannes Meienhofer

  DOI：10.1021/ja00768a070

  日期：1972.6
• Synthesis of the Four Stereoisomeric Forms of α,β-Diaminobutyric Acid and Some Derivatives Suitable for Peptide Synthesis
  作者：Eric Atherton、Johannes Meienhofer

  DOI：10.1515/bchm2.1973.354.2.689

  日期：1973.1
• SN2'-Reactions of Peptide Aziridines. A Cuprate-Based Approach to (E)-Alkene Isosteres
  作者：Peter Wipf、Paul C. Fritch

  DOI：10.1021/jo00096a033

  日期：1994.8

  Alkenylaziridines were prepared from allylic alcohols via Sharpless epoxidation; oxirane to aziridine conversion under modified Staudinger conditions, and Wittig chain extension. Alternatively, beta-hydroxy alpha-amino acids such as threonine can serve as readily available precursors. The corresponding N-acyl, -peptidyl-, -carbamoyl-, and -sulfonylaziridines underwent a high-yielding anti-S(N)2' alkylation with organocopper/BF3 complex to give (E)-alkene peptide isosteres in 62 to >98% de. The stereoselectivity of the addition process was studied by H-1 and F-19 NMR as well as chemical degradation. Alkene isosteres are important nonhydrolyzable and rigidified analogs of peptide bonds in biologically active peptides. This new methodology considerably facilitates the synthesis and the study of these peptide mimetics, since alkenylaziridines are readily prepared and side-chain modification is simplified by the wide range of functionalized organocopper reagents that are available.