(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxy-3-(4,4,5 ,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)phenyl)propanoate | 675832-36-7

• 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: (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxy-3-(4,4,5 ,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)phenyl)propanoate
• 英文别名: Methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)propanoate；methyl (2S)-3-[4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 675832-36-7
• 化学式: C₂₂H₃₄BNO₇
• 分子量: 435.325
• InChiKey: JNFFMSNIGJPWKL-INIZCTEOSA-N

物化性质

• 熔点：
  92-95 °C
• 沸点：
  552.4±50.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxy-3-(4,4,5 ,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)phenyl)propanoate 在 盐酸 、 sodium periodate 、 copper diacetate 、 4 Angstroem MS 、 ammonium acetate 、 水 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 48.0h， 生成 (9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7(19),14,16,17-hexaene
  参考文献：
  名称：

  Synthesis of l,l-cycloisodityrosines by copper(II) acetate-DMAP-mediated intramolecular O-arylation of phenols with phenylboronic acids

  摘要：

  Two types of cycloisodityrosines, 11 and 13, were synthesized from commercially available chiral tyrosine derivatives through the copper(II) acetate-DMAP-mediated diaryl ether formation of boronotyrosyltyrosines 8 and 10, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01390-x
• 作为产物：
  描述：

  L-酪氨酸甲酯盐酸盐 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 碘 、 potassium acetate 、 碳酸氢钠 、 potassium carbonate 、 silver sulfate 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxy-3-(4,4,5 ,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)phenyl)propanoate
  参考文献：
  名称：

  Synthesis and conformation studies of rubiyunnanin B analogs

  摘要：

  Five new analogs 4-8 of rubiyunnanin B (1), mainly modified on the tetrapeptide subunit, were synthesized. These agents 4-8 were substituted D-Ala-L-Ala-L-Tyr(OMe)-L-Ala, D-Ala-L-Ala-L-Phe-L-Ala, D-Ala-L-Ala-L-Tyr-L-Ala, D-Ala-L-Ala-L-Pro-L-Ala, and D-Ala-L-Ala-L-Ala for the D-Ala-L-Ala-c-N-Me-Tyr(OMe)-L-Ala tetrapeptide subunit. Unlike the natural product, the synthetic agents 4-8 adopt only a single solution conformation, and the central peptide bond in the cyclodityrosine subunit of compounds 4-8 adopt trans stereochemistry. Cytotoxic activities of analogs 4-8 against three human cancer cell lines including A549, BGC-823, and HeLa were evaluated and all the five synthesized peptides exhibited no effects against the test cell lines. These compounds were also evaluated for their antiinsulin resistance and insulin sensitizing activities and none of them showed activity in these assays. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.108

文献信息

• [EN] MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES MACROCYCLIQUES À LARGE SPECTRE
  申请人：RQX PHARMACEUTICALS INC

  公开号：WO2018149419A1

  公开（公告）日：2018-08-23

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

  本文提供了抗菌化合物，其中在某些实施例中，这些化合物具有广谱生物活性。在各种实施例中，这些化合物通过抑制细菌类型1信号肽酶（SpsB）发挥作用，这是细菌中的一种必需蛋白质。还提供了使用所述化合物的药物组合物和治疗方法。
• Use of the SPhos Ligand to Suppress Racemization in Arylpinacolboronate Ester Suzuki Couplings Involving α-Amino Acids. Synthesis of Biaryl Derivatives of 4-Hydroxyphenylglycine, Tyrosine, and Tryptophan
  作者：Mònica Prieto、Silvia Mayor、Paul Lloyd-Williams、Ernest Giralt

  DOI：10.1021/jo901899w

  日期：2009.12.4

  α-Amino acid derivatives, particularly those of phenylglycine, can suffer significant racemization in Suzuki couplings. When arylpinacolboronate esters are used as coupling partners this unwanted side reaction can be suppressed by the use of Pd(OAc)2 as Pd(0) source, in the presence of Buchwald’s SPhos ligand. The syntheses of biaryl amino acids of tyrosine, phenylglycine, and tryptophan, including

  α-氨基酸衍生物，特别是苯基甘氨酸的衍生物，在Suzuki偶联中会遭受显着的消旋作用。当芳基频哪醇硼酸酯用作偶联伙伴时，在存在布赫瓦尔德氏SPhos配体的情况下，可以通过使用Pd（OAc）2作为Pd（0）来抑制这种有害的副反应。据报道，酪氨酸，苯基甘氨酸和色氨酸的联芳基氨基酸的合成，包括与天然肽中的氯肽家族相似的Phg-Trp单元。
• Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety
  作者：Iteng Ng-Choi、Àngel Oliveras、Lidia Feliu、Marta Planas

  DOI：10.3762/bjoc.15.72

  日期：——

  A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps. The first one involves the cyclization of a linear peptidyl resin containing the corresponding halo- and boronoamino acids via a microwave-assisted Suzuki–Miyaura cross coupling. This step is followed by the macrolactamization

  已经设计了用于固相合成包含Phe-Phe，Phe-Tyr或Tyr-Tyr基序的联芳基双环肽的方法。该方法包括两个关键步骤。第一个涉及通过微波辅助的Suzuki-Miyaura交叉偶联环化包含相应的卤代和硼酸氨基酸的线性肽基树脂。该步骤之后是所得到的联芳基单环肽基树脂的大内酰胺化，导致形成了预期的联芳基双环肽。这项研究提供了这种双环化合物的首次固相合成，适合于制备各种合成的或天然的双芳基双环肽。
• [EN] BORYLATED AMINO ACID COMPOSITIONS FOR USE IN BORON NEUTRON CAPTURE THERAPY AND METHODS THEREOF<br/>[FR] COMPOSITIONS D'ACIDES AMINÉS BORYLÉS DESTINÉES À ÊTRE UTILISÉES EN THÉRAPIE PAR CAPTURE DE NEUTRONS PAR LE BORE ET MÉTHODES ASSOCIÉES
  申请人：TAE LIFE SCIENCES

  公开号：WO2020180390A1

  公开（公告）日：2020-09-10

  Borylated Amino Acid ("BAA") compositions and methods of making BAAs are disclosed herein. Consequently, the BAAs can be administered to patients as a Neutron Capture Agent and provide a method of treating cancer, immunological disorders and other disease by utilizing a Neutron Capture Therapy modality.

  本文披露了硼化氨基酸（“BAA”）组合物及制备BAA的方法。因此，可以将BAA用作中子俘获剂向患者施用，并提供了一种利用中子俘获治疗模式治疗癌症、免疫性疾病和其他疾病的方法。
• Solid-phase synthesis of biaryl cyclic peptides containing a histidine-tyrosine linkage
  作者：Iteng Ng-Choi、Àngel Oliveras、Marta Planas、Lidia Feliu

  DOI：10.1016/j.tet.2019.03.014

  日期：2019.5

  A solid-phase strategy for the synthesis of biaryl cyclic peptides containing a side-chain to side-chain His-Tyr linkage was developed. The key step was the macrocyclization of a linear peptidyl resin incorporating a 5-bromohistidine and a 3-boronotyrosine via the formation of the biaryl bond by means of a microwave-assisted Suzuki-Miyaura reaction. This method allowed direct access to biaryl cyclic

  开发了一种固相策略，用于合成包含侧链至侧链His-Tyr连接的联芳基环肽。关键步骤是通过微波辅助的Suzuki-Miyaura反应通过形成联芳基键合并入5-溴组氨酸和3-硼代酪氨酸的线性肽基树脂的大环化。该方法允许直接获得含有3或5个氨基酸环并在N端或C端带有组氨酸残基的联芳基环肽，特别有利于该氨基酸位于C端的类似物。总站。这项研究还有助于建立一种策略，用于合成衍生自天然联芳基双环肽aciculitins的两个半球的联芳基环肽。