ethyl (2S)-2-(benzylideneamino)-2-[3-[5-(1,3-dithian-2-yl)-2-methoxyphenoxy]-5-methoxyphenyl]acetate | 143145-60-2

• 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: ethyl (2S)-2-(benzylideneamino)-2-[3-[5-(1,3-dithian-2-yl)-2-methoxyphenoxy]-5-methoxyphenyl]acetate
• CAS: 143145-60-2
• 化学式: C₂₉H₃₁NO₅S₂
• 分子量: 537.701
• InChiKey: LFYQQEQTIJEOMW-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl (2S)-2-(benzylideneamino)-2-[3-[5-(1,3-dithian-2-yl)-2-methoxyphenoxy]-5-methoxyphenyl]acetate 在 palladium on activated charcoal lead(IV) acetate 、 盐酸 、 四丁基氟化铵 、 氢气 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， 反应 66.58h， 生成 N-D-tyrosyl-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>amino-<(pentafluorophenoxy)carbonyl>methyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester hydrochloride
  参考文献：
  名称：

  Studies directed toward the synthesis of glycopeptide antibiotic teicoplanin: first synthesis of the N-terminal 14-membered ring

  摘要：

  The N-terminal 14-membered ring formed by an ether linkage between the phenyl moieties of amino acids 1 and 3 of glycopeptide antibiotic teicoplanin 1 plays a crucial role in binding of C-terminal D-Ala-D-Ala residues of the peptidoglycan precursor, thereby inhibiting bacterial cell wall biosynthesis. Herein, the first stereocontrolled synthesis of this very important cyclic peptide 2 is described. The two alpha-arylglycines present in this segment are constructed in optically pure form by diastereoselective Strecker synthesis using alpha-phenylglycinol as chiral auxiliary. Finally, the coupling between the acid function of amino acid 1 and the amino function of amino acid 2 leads to the desired macrocyclization. Optical purity of the synthetic product is determined by NMR studies.

  DOI：

  10.1021/jo00046a031
• 作为产物：
  描述：

  3,5-二羟基苯甲酸 在 lead(IV) acetate 、 盐酸 、 甲醇 、 硫酸 、 三氟化硼乙醚 、 四丁基碘化铵 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 反应 27.66h， 生成 ethyl (2S)-2-(benzylideneamino)-2-[3-[5-(1,3-dithian-2-yl)-2-methoxyphenoxy]-5-methoxyphenyl]acetate
  参考文献：
  名称：

  Studies directed toward the synthesis of glycopeptide antibiotic teicoplanin: first synthesis of the N-terminal 14-membered ring

  摘要：

  The N-terminal 14-membered ring formed by an ether linkage between the phenyl moieties of amino acids 1 and 3 of glycopeptide antibiotic teicoplanin 1 plays a crucial role in binding of C-terminal D-Ala-D-Ala residues of the peptidoglycan precursor, thereby inhibiting bacterial cell wall biosynthesis. Herein, the first stereocontrolled synthesis of this very important cyclic peptide 2 is described. The two alpha-arylglycines present in this segment are constructed in optically pure form by diastereoselective Strecker synthesis using alpha-phenylglycinol as chiral auxiliary. Finally, the coupling between the acid function of amino acid 1 and the amino function of amino acid 2 leads to the desired macrocyclization. Optical purity of the synthetic product is determined by NMR studies.

  DOI：

  10.1021/jo00046a031

文献信息

• Studies directed toward the synthesis of glycopeptide antibiotic teicoplanin: first synthesis of the N-terminal 14-membered ring
  作者：T. K. Chakraborty、G. Venkat Reddy

  DOI：10.1021/jo00046a031

  日期：1992.9

  The N-terminal 14-membered ring formed by an ether linkage between the phenyl moieties of amino acids 1 and 3 of glycopeptide antibiotic teicoplanin 1 plays a crucial role in binding of C-terminal D-Ala-D-Ala residues of the peptidoglycan precursor, thereby inhibiting bacterial cell wall biosynthesis. Herein, the first stereocontrolled synthesis of this very important cyclic peptide 2 is described. The two alpha-arylglycines present in this segment are constructed in optically pure form by diastereoselective Strecker synthesis using alpha-phenylglycinol as chiral auxiliary. Finally, the coupling between the acid function of amino acid 1 and the amino function of amino acid 2 leads to the desired macrocyclization. Optical purity of the synthetic product is determined by NMR studies.