methyl N-tert-butyloxycarbonyl-L-(4-trimethylstannylphenyl)alaninate

• 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: methyl N-tert-butyloxycarbonyl-L-(4-trimethylstannylphenyl)alaninate
• 英文别名: N-Boc-4-trimethylstannyl-L-phenylalanine methyl ester；N-tert-butyloxycarbonyl-(L)-4-(trimethylstannyl)phenylalanine methyl ester；(S)-2-tert-butoxycarbonylamino-3-(4-trimethylstannylphenyl) propionic acid methyl ester；methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-trimethylstannylphenyl)propanoate
• 化学式: C₁₈H₂₉NO₄Sn
• 分子量: 442.143
• InChiKey: FSGJCLFOHJAAAO-KCOFNFEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  n-叔丁氧基羰基-3-(4-联苯)-2-氨基丙酸-(S)-甲酯	methyl (S)-3-([1,1'-biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoate	137255-86-8	C21H25NO4	355.434
  ——	Boc-4-(4-methylphenyl)phenylalanine methyl ester	137255-87-9	C22H27NO4	369.461
  ——	(S)-methyl α-{[(1,1-dimethylethoxy)carbonyl]amino}-4'-chloro(1,1'-biphenyl)-4-propanoate	137255-88-0	C21H24ClNO4	389.879
  ——	(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4'-methoxybiphenyl-4-yl)propanoate	196395-09-2	C22H27NO5	385.46
  ——	N-(t-butyloxycarbonyl)-4-(1-naphthyl)-L-phenylalanine methyl ester	137255-89-1	C25H27NO4	405.494
  ——	N-tert-butoxycarbonyl-4-(pyridin-3-yl)-L-phenylalanine methyl ester	193420-27-8	C20H24N2O4	356.422
  ——	N-tert-Butyloxycarbonyl-(L)4-(2'-cyanophenyl)phenylalanine Methyl Ester	390382-08-8	C22H24N2O4	380.444

反应信息

• 作为反应物：
  描述：

  methyl N-tert-butyloxycarbonyl-L-(4-trimethylstannylphenyl)alaninate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 氯化亚砜 、 三苯胂 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 (S)-2-Amino-3-(4-naphthalen-1-yl-phenyl)-propionic acid methyl ester
  参考文献：
  名称：

  An Efficient Synthesis of 4-Aryl and 4-Vinylphenylalanines by Stille Cross-Coupling Reaction

  摘要：

  在钯催化下，N-叔丁氧羰基-4-三甲基锡-L-苯丙氨酸甲酯（1）与多种芳基和乙烯基碘化物和三酸盐（2）发生反应，生成相应的 4-芳基和 4-乙烯基苯丙氨酸 3，合成产率高。

  DOI：

  10.1055/s-0030-1260179

文献信息

• Multicyclic compounds which inhibit leukocyte adhesion mediated by VLA-4
  申请人：Elan Pharmaceuticals, Inc.

  公开号：US06465513B1

  公开（公告）日：2002-10-15

  Disclosed are compounds which bind VLA-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

  本文披露了与VLA-4结合的化合物。其中某些化合物还抑制白细胞粘附，尤其是由VLA-4介导的白细胞粘附。这些化合物在治疗哺乳动物患者（例如人类）的炎症性疾病中很有用，如哮喘、阿尔茨海默病、动脉粥样硬化、艾滋病痴呆、糖尿病、炎症性肠病、类风湿关节炎、组织移植、肿瘤转移和心肌缺血。这些化合物还可用于治疗多发性硬化等炎症性脑部疾病。
• Copper-Mediated Aromatic Radiofluorination Revisited: Efficient Production of PET Tracers on a Preparative Scale
  作者：Boris D. Zlatopolskiy、Johannes Zischler、Philipp Krapf、Fadi Zarrad、Elizaveta A. Urusova、Elena Kordys、Heike Endepols、Bernd Neumaier

  DOI：10.1002/chem.201405586

  日期：2015.4.7

  Two novel methods for copper‐mediated aromatic nucleophilic radiofluorination were recently reported. Evaluation of these methods reveals that, although both are efficient in small‐scale experiments, they are inoperative for the production of positron emission tomography (PET) tracers. Since high base content turned out to be responsible for low radiochemical conversions, a “low base” protocol has

  最近报道了两种铜介导的芳香族亲核放射性氟化的新方法。对这些方法的评估表明，尽管这两种方法在小规模实验中都是有效的，但它们对于生产正电子发射断层扫描（PET）示踪剂是无效的。由于事实证明高碱含量是造成低放射性化学转化的原因，因此开发了一种“低碱”方案，该方案可从二芳基碘鎓盐和芳基频哪醇硼酸酯中以合理的产率提供18 F标记的芳烃。此外，实施我们的“极简主义”方法来处理（间苯二甲酰基）（芳基）碘鎓盐的铜介导的[ 18 F]-氟化反应，可以制备18具有出色RCC的F标签芳烃。新颖的放射性氟化方法避免了费时的共沸干燥，并且避免了利用碱和其他添加剂（例如穴状配体）。此外，该程序可以生产临床相关的PET示踪剂。[ 18 F] FDA，4- [ 18 F] FPhe和[ 18 F] DAA1106以良好的分离放射化学产率获得。此外，[ 18 F] DAA1106已在大鼠中风模型中进行了评估，并证明了可视化
• Synthesis and binding studies of two new macrocyclic receptors for the stereoselective recognition of dipeptides
  作者：Ana Maria Castilla、M Morgan Conn、Pablo Ballester

  DOI：10.3762/bjoc.6.5

  日期：——

  We present here the design, synthesis, and analysis of a series of receptors for peptide ligands inspired by the hydrogen-bonding pattern of protein β-sheets. The receptors themselves can be regarded as strands 1 and 3 of a three-stranded β-sheet, with cross-linking between the chains through the 4-position of adjacent phenylalanine residues. We also report on the conformational equilibria of these receptors in solution as well as on their tendency to dimerize. ¹H NMR titration experiments are used to quantify the dimerization constants, as well as the association constant values of the 1:1 complexes formed between the receptors and a series of diamides and dipeptides. The receptors show moderate levels of selectivity in the molecular recognition of the hydrogen-bonding pattern present in the diamide series, selecting the α-amino acid-related hydrogen-bonding functionality. Only one of the two cyclic receptors shows modest signs of enantioselectivity and moderate diastereoselectivity in the recognition of the enantiomers and diastereoisomers of the Ala-Ala dipeptide (ΔΔG⁰₁ (DD-DL) = −1.08 kcal/mol and ΔΔG⁰₁ (DD-LD) = −0.89 kcal/mol). Surprisingly, the linear synthetic precursors show higher levels of stereoselectivity than their cyclic counterparts.

  我们在这里介绍了一系列受蛋白质β-折叠中氢键模式启发的肽配体受体的设计、合成和分析。这些受体本身可以被视为一个三股β-折叠中的第一股和第三股，通过相邻苯丙氨酸残基的4位交联链之间的交联。我们还报告了这些受体在溶液中的构象平衡以及它们二聚的倾向。使用1H NMR滴定实验来量化二聚化常数，以及受体和一系列二酰胺和二肽形成的1:1复合物的关联常数值。这些受体在分子识别二酰胺系列中存在的氢键模式方面表现出适度的选择性，选择α-氨基酸相关的氢键功能。仅有两个环状受体中的一个显示出对Ala-Ala二肽的对映体和对映异构体的识别中适度的对映选择性和中等的顺反异构选择性（ΔΔG01（DD-DL）= -1.08 kcal/mol和ΔΔG01（DD-LD）= -0.89 kcal/mol）。令人惊讶的是，线性合成前体显示出比它们的环状对应物更高的立体选择性。
• Urea derivatives as integrin alpha 4 antagonists
  申请人：——

  公开号：US20040142982A1

  公开（公告）日：2004-07-22

  Novel antagonists of ∝4&bgr;1 integrin and/or ∝4&bgr;7 integrin of the general Formula I: wherein R1, R2, R5, L1, L2, Rb, W and Z are as defined in any one of claims 1 to 13, A represents —CH— or a nitrogen atom, and p is from 0 to 4.

  通用公式I的小说拮抗剂为∝4&bgr;1整合素和/或∝4&bgr;7整合素，其中R1、R2、R5、L1、L2、Rb、W和Z的定义如权利要求1至13中的任何一个，A代表—CH—或氮原子，p为0到4。
• Urea derivatives as integrin α4 antagonists
  申请人：Laboratorios Almirall, S.A.

  公开号：US07253171B2

  公开（公告）日：2007-08-07

  Novel antagonists of ∝4β1 integrin and/or ∝4β7 integrin of the general Formula I: wherein R1, R2, R5, L1, L2, Rb, W and Z are as defined in any one of claims 1 to 13, A represents —CH— or a nitrogen atom, and p is from 0 to 4.

  通用公式I的新型α4β1整合素和/或α4β7整合素拮抗剂：其中R1、R2、R5、L1、L2、Rb、W和Z的定义如权利要求1至13中的任意一个所述，A表示—CH—或氮原子，p为0至4。