O-acetyl-N-phthaloyl-L-tyrosine methyl ester | 160648-53-3

• 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: O-acetyl-N-phthaloyl-L-tyrosine methyl ester
• 英文别名: methyl (2S)-3-(4-acetyloxyphenyl)-2-(1,3-dioxoisoindol-2-yl)propanoate
• CAS: 160648-53-3
• 化学式: C₂₀H₁₇NO₆
• 分子量: 367.358
• InChiKey: RXDUEMOLZTWIFG-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.98
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  O-acetyl-N-phthaloyl-L-tyrosine methyl ester 生成 (2S)-O-acetyl-3-bromo-N-phthaloyltyrosine methyl ester
  参考文献：
  名称：

  EASTON, CHRISTOPHER J.;HUTTON, CRAIG A.;ENG, WUI TAN;TIEKINK, EDWARD R. T+, TETRAHEDRON LETT., 31,(1990) N8, C. 7059-7062

  摘要：

  DOI：
• 作为产物：
  描述：

  苯酐 在 acid 作用下， 生成 O-acetyl-N-phthaloyl-L-tyrosine methyl ester
  参考文献：
  名称：

  Synthesis of homochiral hydroxy-α-amino acid derivatives

  摘要：

  DOI：

  10.1016/s0040-4039(00)97242-3

文献信息

• Total Synthesis of Dynobactin A
  作者：Fabian Schneider、Yinliang Guo、You-Chen Lin、Kelly J. Eberle、Debora Chiodi、Johnathan A. Greene、Chenxin Lu、Phil S. Baran

  DOI：10.1021/jacs.3c11560

  日期：2024.3.13

  The first total synthesis of the potent antimicrobial agent dynobactin A is disclosed. This synthesis enlists a singular aziridine ring opening strategy to access the two disparate β-aryl-branched amino acids present within this complex decapeptide. Featuring a number of unique maneuvers to navigate inherently sensitive and epimerizable functional groups, this convergent approach proceeds in only 16

  首次公开了强效抗菌剂 Dynobactin A 的全合成。该合成采用单一的氮丙啶开环策略来接触该复杂十肽中存在的两个不同的 β-芳基支链氨基酸。这种聚合方法具有许多独特的操作来导航固有敏感和差向异构的官能团，从商业材料中仅需要 16 个步骤 (LLS)，并且应该有助于合成用于药物化学研究的众多类似物。
• Stereocontrolled synthesis of β-hydroxyphenylalanine and β-hydroxytyrosine derivatives
  作者：Christopher J. Easton、Craig A. Hutton、Peter D. Roselt、Edward R.T. Tiekink

  DOI：10.1016/s0040-4020(01)85256-x

  日期：1994.1

  Side-chain bromination of N-phthaloyl-(S)-phenylalanine and tyrosine derivatives, followed by treatment of the product bromides with silver nitrate in aqueous acetone, affords the corresponding (2S,3R)-beta-hydroxy-alpha-amino acids, enantiospecifically and diastereoselectively. The diastereoselectivity depends on the carboxyl protecting group, tert-Butyl esters display greater stereoselectivity than the corresponding methyl esters, presumably as a result of a steric effect, while N-tert-butylamides react diastereospecifically due to a combination of steric and electronic effects.
• Concise Synthesis of All Stereoisomers of β-Methoxytyrosine and Determination of the Absolute Configuration of the Residue in Callipeltin A
  作者：Angela Zampella、Rosa D'Orsi、Valentina Sepe、Agostino Casapullo、Maria Chiara Monti、Maria Valeria D'Auria

  DOI：10.1021/ol0513600

  日期：2005.8.1

  All stereoisomers of beta-methoxytyrosine (beta-OMeTyr), a stereo-undefined component of callipeltin A, were synthesized from L- and D-tyrosine. The stereochemistry of beta-OMeTyr in callipeltin A was determined to be 2R,3R by an oxidative procedure and Marfey's analysis.