L-BOC-Tyr-OC6F5 | 113807-07-1

• 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: L-BOC-Tyr-OC6F5
• 英文别名: Boc-Tyr-OPfp；(2,3,4,5,6-pentafluorophenyl) (2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 113807-07-1
• 化学式: C₂₀H₁₈F₅NO₅
• 分子量: 447.359
• InChiKey: OSCDYOGDCDLCAZ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 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：
  10

反应信息

• 作为反应物：
  描述：

  L-BOC-Tyr-OC6F5 在 palladium on activated charcoal copper(I) oxide 、 盐酸 、 tetrafluoroboric acid 、 亚硝酸特丁酯 、 氢气 、 sodium hydride 、 碳酸氢钠 、 copper(II) nitrate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 methyl 12(S)-amino-4-methoxy-11-oxo-10-aza-2-oxatricyclo<12.2.2.1^3,7>-nonadeca-3,5,7(19),14,16,17-hexaene-9(S)-carboxylate
  参考文献：
  名称：

  Synthesis of (9S,12S)-cycloisodityrosine and its unnatural (9R,12S)-diastereomer

  摘要：

  A synthesis of the (9S,12S)-cycloisodityrosine derivatives and their unnatural (9R,12S)-diastereomers are disclosed. The approach is based on an intramolecular aromatic nucleophilic substitution reaction for formation of the macrocyclic biaryl ether and includes the documentation of a remarkably facile base-catalyzed epimerization. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00179-5
• 作为产物：
  描述：

  五氟苯酚 、 Boc-L-酪氨酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到L-BOC-Tyr-OC6F5
  参考文献：
  名称：

  Synthesis of (9S,12S)-cycloisodityrosine and its unnatural (9R,12S)-diastereomer

  摘要：

  A synthesis of the (9S,12S)-cycloisodityrosine derivatives and their unnatural (9R,12S)-diastereomers are disclosed. The approach is based on an intramolecular aromatic nucleophilic substitution reaction for formation of the macrocyclic biaryl ether and includes the documentation of a remarkably facile base-catalyzed epimerization. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00179-5

文献信息

• Synthesis of (9<i>R</i>,12<i>S</i>)- and (9<i>S</i>,12<i>S</i>)-Cycloisodityrosine and Their <i>N</i>-Methyl Derivatives
  作者：Dale L. Boger、Jiacheng Zhou、Robert M. Borzilleri、Seiji Nukui、Steven L. Castle

  DOI：10.1021/jo961346o

  日期：1997.4.1

  Full details of the synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives are detailed based on an intramolecular nucleophilic aromatic substitution reaction for formation of the key biaryl ether with 14-membered ring macrocyclization. Their comparison with prior samples and the documentation of a facile C9 epimerization within the natural 9S series are described.

  基于分子内亲核芳族取代反应以形成具有14元环大环化的关键联芳基醚，详细描述了（9R，12S）-和（9S，12S）-环异酪氨酸及其N-甲基衍生物的合成的详细信息。描述了它们与先前样品的比较以及天然9S系列中C9差向异构酶的简便记录。
• Acetol: a useful new protecting group for peptide synthesis
  作者：Bijoy Kundu

  DOI：10.1016/s0040-4039(00)79849-2

  日期：1992.5

  Acetol can be conveniently used as a reagent for the protection of carboxylic acids in peptide synthesis. It has been found to be inert and stable to hydrogenolytic and acidolytic conditions normally used in peptide synthesis. Deblocking has been selectively achieved under mild conditions using Bu4NF.3H2O in THF.

  乙炔可以方便地用作肽合成中保护羧酸的试剂。已经发现它对通常用于肽合成的氢解和酸解条件是惰性的和稳定的。在温和条件下使用THF中的Bu 4 NF.3H 2 O选择性地实现了解封闭。
• AXREM, A. A.;MARTINOVICH, V. P.;GOLUBOVICH, V. P.;KAMENSKIJ, A. A.;BATURI+, VESTSI AN BSSR. CEP. XIM. N.,(1989) N, S. 58-63
  作者：AXREM, A. A.、MARTINOVICH, V. P.、GOLUBOVICH, V. P.、KAMENSKIJ, A. A.、BATURI+

  DOI：——

  日期：——
• Synthesis of (9S,12S)-cycloisodityrosine and its unnatural (9R,12S)-diastereomer
  作者：Dale L. Boger、Jiacheng Zhou、Robert M. Borzilleri、Seiji Nukui

  DOI：10.1016/0960-894x(96)00179-5

  日期：1996.5

  A synthesis of the (9S,12S)-cycloisodityrosine derivatives and their unnatural (9R,12S)-diastereomers are disclosed. The approach is based on an intramolecular aromatic nucleophilic substitution reaction for formation of the macrocyclic biaryl ether and includes the documentation of a remarkably facile base-catalyzed epimerization. (C) 1996 Elsevier Science Ltd