(2S,3R)-N-(tert-butyloxycarbonyl)-3-methoxyphenylalanine | 753487-55-7

• 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: (2S,3R)-N-(tert-butyloxycarbonyl)-3-methoxyphenylalanine
• 英文别名: (2S,3R)-N-Boc-3-methoxyphenylalanine；(2S,3R)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid
• CAS: 753487-55-7
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: NSYXJPSTLLXQSN-NWDGAFQWSA-N

物化性质

• 沸点：
  441.1±45.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (2S,3R)-N-(tert-butyloxycarbonyl)-3-methoxyphenylalanine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 H-Phe(bR-OMe)-Val-N(Me)Leu-Oallyl
  参考文献：
  名称：

  Total Synthesis of Cyclomarin C

  摘要：

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.

  DOI：

  10.1021/ol049065n
• 作为产物：
  描述：

  (2R,3R)-N-Boc-3-methoxy-1-O-(tert-butyldimethylsilyl)-phenylalaninol 在 sodium chlorite 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 乙腈 为溶剂， 反应 20.0h， 生成 (2S,3R)-N-(tert-butyloxycarbonyl)-3-methoxyphenylalanine
  参考文献：
  名称：

  Synthesis of modified β-methoxyphenylalanines via diazonium chemistry and their incorporation in desoxycyclomarin analogues

  摘要：

  氯霉素基础物质转化为取代的syn-β-甲氧基苯丙氨酸，这是改良环海菌素的构建块。

  DOI：

  10.1039/c8ob02777c

文献信息

• Total synthesis of cyclomarins A, C and D, marine cyclic peptides with interesting anti-tuberculosis and anti-malaria activities
  作者：Philipp Barbie、Uli Kazmaier

  DOI：10.1039/c6ob00800c

  日期：——

  Cyclomarins are cyclic heptapeptides containing four unusual amino acids. New synthetic protocols toward their synthesis have been developed, leading to the synthesis and biological evaluation of three natural occurring cyclomarins. Interestingly, cyclomarins address two completely different targets: Clp C1, a subunit of the caseinolytic protease of Mycobacterium tuberculosis (MTB), as well as PfAp3Ase

  环豆素是含有四个不同氨基酸的环状七肽。已经开发出用于其合成的新的合成方案，从而导致了三种天然存在的环烷的合成和生物学评估。有趣的是，水手素针对两个完全不同的靶标：Clp C1，结核分枝杆菌（MTB）的酪蛋白水解蛋白酶的亚基，以及恶性疟原虫的PfAp 3 Ase 。因此，对于开发抗结核和疟疾药物而言，水手素是有趣的先导结构。
• Macrocyclization studies and total synthesis of cyclomarin C, an anti-inflammatory marine cyclopeptide
  作者：Shi-Jun Wen、Tai-Shan Hu、Zhu-Jun Yao

  DOI：10.1016/j.tet.2005.03.058

  日期：2005.5

  The studies on macrocyclization at possible sites toward the total synthesis of cyclomarin C are described. The results showed that both Trp and Phe derivatives involved in the target could not be the terminals of the final linear peptide precursors. Additionally, preparation of corresponding dipeptides with an N-methyl amide bond is not favorable in the synthesis of linear precursors. Site d was finally proved a proper site for the cyclopeptide formation, and the corresponding head-to-tail macrocyclization was achieved under mild conditions and gave repeatable and satisfactory yields. (c) 2005 Elsevier Ltd. All rights reserved.
• Total Synthesis of Cyclomarin A, a Marine Cycloheptapeptide with Anti-Tuberculosis and Anti-Malaria Activity
  作者：Philipp Barbie、Uli Kazmaier

  DOI：10.1021/acs.orglett.5b03292

  日期：2016.1.15

  An efficient synthetic protocol for the stereoselective synthesis of cyclomarin A is reported. Key steps in the syntheses of the building blocks are an asymmetric chelate-enolate Claisen rearrangement, an asymmetric hydrogenation, and highly diastereoselective additions of organozinc and -titanium reagents.
• Synthesis of modified β-methoxyphenylalanines <i>via</i> diazonium chemistry and their incorporation in desoxycyclomarin analogues
  作者：Alexander Kiefer、Uli Kazmaier

  DOI：10.1039/c8ob02777c

  日期：——

  Chloramphenicol base is converted into substituted syn-β-methoxyphenylalanins, building blocks of modified cyclomarins.

  氯霉素基础物质转化为取代的syn-β-甲氧基苯丙氨酸，这是改良环海菌素的构建块。
• Total Synthesis of Cyclomarin C
  作者：Shi-Jun Wen、Zhu-Jun Yao

  DOI：10.1021/ol049065n

  日期：2004.8.1

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.