N-(tert-butyloxycarbonyl)-D-4-hydroxyphenylglycine benzyl ester | 130761-80-7

• 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-(tert-butyloxycarbonyl)-D-4-hydroxyphenylglycine benzyl ester
• 英文别名: benzyl (2R)-2-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 130761-80-7
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: QQHAEOZYEYJWBR-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(tert-butyloxycarbonyl)-D-4-hydroxyphenylglycine benzyl ester 在 palladium on activated charcoal 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.25h， 生成 N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-4-hydroxyphenylglycine
  参考文献：
  名称：

  Synthesis and siderophore activity of albomycin-like peptides derived from N5-acetyl-N5-hydroxy-L-ornithine

  摘要：

  N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23 % yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid. Reduction of 6 to 7 and treatment with N-[(trichloroethoxy)carbonyl]-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g). Following alpha-amino and alpha-carboxyl deprotections of 11 and 12, EEDQ [2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline] mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36). The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5). These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.

  DOI：

  10.1021/jm00107a013
• 作为产物：
  描述：

  N-Boc-R-对羟基苯甘氨酸 以58%的产率得到
  参考文献：
  名称：

  DOLENCE, E. KURT.;LIN, CHIA-EN;MILLER, MARVIN J.;PAYNE, SHELLEY M., J. MED. CHEM., 34,(1991) N, C. 956-968

  摘要：

  DOI：

文献信息

• Substituted hydantoins
  申请人：Chu Xin-Jie

  公开号：US20060041146A1

  公开（公告）日：2006-02-23

  The present invention relates to compounds of the formula which are useful in treating diseases characterized by the hyperactivity of MEK. Accordingly the compounds are useful in the treatment of diseases, such as, cancer, cognative and CNS disorders and inflammatory/autoimmune diseases.

  本发明涉及一类化合物，其结构式如下： 这些化合物在治疗由MEK过度活跃引起的疾病方面具有用途。因此，这些化合物在治疗诸如癌症、认知和CNS疾病以及炎症/自身免疫疾病等疾病方面是有用的。
• Synthesis of heterodisaccharide-containing peptides, fragments of actinoidin antibiotics
  作者：Carole Mouton、François Tillequin、Elisabeth Seguin、Claude Monneret

  DOI：10.1039/a802053a

  日期：——

  Prototypes corresponding to glycopeptide fragments of actinoidin antibiotics have been synthesized using an L-acosaminyl-D-glucose-containing heterodisaccharide linked to 4-hydroxyphenylglycine as pivotal synthon. This latter compound has been obtained by coupling of a suitably protected D-glucopyranosyl bromide with the blocked amino acid, followed by selective deprotection of the glucopyranosyl moiety at C-2 and subsequent stereospecific attachment of the acosaminyl unit.

  与抗生素作用素片段对应的原型已经合成，使用了一个含有L-阿克萨糖胺-D-葡萄糖的异二糖，该异二糖连接在4-羟基苯基甘氨酸上，作为关键合成单元。后者化合物是通过将适当保护的D-葡萄糖吡喃基溴化物与被阻断的氨基酸偶联得到的，随后选择性去保护C-2位的葡萄糖吡喃基部分，并随后立体特异性地连接阿克萨糖胺单元。
• DOLENCE, E. KURT.;LIN, CHIA-EN;MILLER, MARVIN J.;PAYNE, SHELLEY M., J. MED. CHEM., 34,(1991) N, C. 956-968
  作者：DOLENCE, E. KURT.、LIN, CHIA-EN、MILLER, MARVIN J.、PAYNE, SHELLEY M.

  DOI：——

  日期：——
• SUBSTITUTED HYDANTOINS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1781649B1

  公开（公告）日：2008-08-13
• US7427635B2
  申请人：——

  公开号：US7427635B2

  公开（公告）日：2008-09-23