Z-Phg-F | 133010-29-4

• 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: Z-Phg-F
• 英文别名: benzyl N-[(1S)-2-fluoro-2-oxo-1-phenylethyl]carbamate
• CAS: 133010-29-4
• 化学式: C₁₆H₁₄FNO₃
• 分子量: 287.29
• InChiKey: FYZRZSWGDPBGDW-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-酞酰亚胺基丙酸甲酯 、 Z-Phg-F 以75%的产率得到
  参考文献：
  名称：

  CARPINO, LOUIS A.;MANSOUR, EL-SAYED M. E.;SADAT-AALAEE, DEAN, J. ORG. CHEM., 56,(1991) N, C. 2611-2614

  摘要：

  DOI：
• 作为产物：
  描述：

  Cbz-L-苯甘氨酸 在 N,N-二异丙基乙胺 、 fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 作用下， 以69%的产率得到Z-Phg-F
  参考文献：
  名称：

  Tetramethylfluoroformamidinium Hexafluorophosphate: A Rapid-Acting Peptide Coupling Reagent for Solution and Solid Phase Peptide Synthesis

  摘要：

  DOI：

  10.1021/ja00124a040

文献信息

• Suresh Babu; Gopi; Ananda, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 5, p. 384 - 386
  作者：Suresh Babu、Gopi、Ananda

  DOI：——

  日期：——
• Stepwise Automated Solid Phase Synthesis of Naturally Occurring Peptaibols Using FMOC Amino Acid Fluorides
  作者：Holger Wenschuh、Michael Beyermann、Hanka Haber、Joachim K. Seydel、Eberhard Krause、Michael Bienert、Louis A. Carpino、Ayman El-Faham、Fernando Albericio

  DOI：10.1021/jo00107a020

  日期：1995.1

  The standard methods of stepwise solid phase synthesis according to Merrifield could not previously be applied to the synthesis of the important naturally occurring peptaibols because of difficulties arising from the pronounced steric hindrance caused by alpha,alpha-dialkylated amino acids (incomplete coupling, especially to adjacent similarly constituted units, racemization due to slow coupling to hindered amino acids, etc.), chain degradation due to the presence of acid-labile Aib-Pro linkages, and the lack of any general method for the loading of C-terminal amino alcohols to resin supports. Following recent work on model systems, it is now shown that the adoption of Fmoc amino acid fluorides as coupling reagents makes possible the facile, general assembly of such peptides. The method was demonstrated for alamethicin F30 and F50, saturnisporin SA III, and trichotoxin A50-J. The crude products were of remarkable purity. Amino acid analysis, mass spectral data, and comparison of the synthetic alamethicins with samples of naturally occurring material confirmed the success of the syntheses. No significant amount of racemization (<0.8%) was found for any of the chiral amino acids present. The first step of the synthesis involved a new general method for assembly of C-terminal peptide alcohols via the use of 0-chlorotrityl resin. In addition, model studies on the question of racemization during the coupling of Fmoc amino acid fluorides are reported.