methyl (2R)-2-[(tert-butoxy)carbonylamino]-4-hydroxybutanoate

• 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 (2R)-2-[(tert-butoxy)carbonylamino]-4-hydroxybutanoate
• 英文别名: methyl (R)-2[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate；(R)-Methyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate；methyl (2R)-4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• 化学式: C₁₀H₁₉NO₅
• 分子量: 233.265
• InChiKey: IWNVPOPPBRMFNG-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  methyl (2R)-2-[(tert-butoxy)carbonylamino]-4-hydroxybutanoate 在 甲基磺酰氯 、 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 15.5h， 以82%的产率得到methyl (2R)-<(tert-butyloxycarbonyl)amino>-4-bromobutyrate
  参考文献：
  名称：

  Synthesis of fluorinated analogues of sphingosine-1-phosphate antagonists as potential radiotracers for molecular imaging using positron emission tomography

  摘要：

  Sphingosine-1-phosphate (S1P) receptors play major roles in cardiovascular, immunological and neurological diseases. The recent approval of the sphingolipid drug Fingolimod (Gilenya®), a sphingosine-1-phosphate agonist for relapsing multiple sclerosis, in 2010 exemplifies the potential for targeting sphingolipids for the treatment of human disorders. Moreover, non-invasive in vivo imaging of S1P receptors that are not available till now would contribute to the understanding of their role in specific pathologies and is therefore of preclinical interest. Based on fluorinated analogues of the S1P1 receptor antagonist W146 showing practically equal in vitro potency as the lead structure, the first S1P receptor antagonist [18F]-radiotracer has been synthesized and tested for in vivo imaging of the S1P1 receptor using positron emission tomography (PET). Though the tracer is serum stable, initial in vivo images show fast metabolism and subsequent accumulation of free [18F]fluoride in the bones.

  DOI：

  10.1016/j.bmc.2014.08.009
• 作为产物：
  描述：

  (R)-2,2-二甲基-3-(n-boc)-4-乙炔噁唑啉 在 chromium(VI) oxide 、 palladium on activated charcoal 过氧乙酸 、 氢气 、 potassium acetate 、 potassium hydrogencarbonate 、 高碘酸 、 三氟乙酸 、 potassium bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 12.5h， 生成 methyl (2R)-2-[(tert-butoxy)carbonylamino]-4-hydroxybutanoate
  参考文献：
  名称：

  Silylcupration of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine:  A Stereoselective Approach to the Synthesis of γ-Silylated Saturated and Unsaturated α-Amino Acids

  摘要：

  Enantioselective synthesis of gamma-silylated amino acids is reported, using a four-step procedure based on the silylcupration of ethynyloxazolidine 2. Silylcuprates 6a-c are highlighted as useful reagents to be employed with enantiomerically enriched substrates. Vinylsilanes 5 are easily prepared and highlighted as useful intermediates to yield the final-compounds after reduction, opening of the oxazolidine ring, and oxidation. Moreover, beta,gamma-unsaturated amino acids are obtained as very interesting vinylglycine derivatives. The capability of silicon-containing amino acids to be incorporated into dipeptides is also shown.

  DOI：

  10.1021/jo991272r

文献信息

• Synthesis of purpuroine A, nakirodin A and MDN-0104: The hidden puzzles and risk of error in their configurational assignments
  作者：Wen-Ju Wu、Yikang Wu、Bo Liu

  DOI：10.1016/j.tet.2017.01.029

  日期：2017.3

  The unusual (R) configuration previously assigned (with seemingly undoubted evidence) to purpuroin A and nakirodin A was disproved by synthesis. The optical rotation and NMR data for structure assigned for salt-free nakirodin A were made available for the first time. The difficulty and potential risk of error in configurational assignments of diastereomers for remote stereocenters were exemplified

  通过合成证明了先前分配给紫癜素A和那奇罗定A的异常（R）构型（貌似毫无疑问）。首次提供了分配给无盐那奇罗汀A的结构的旋光度和NMR数据。通过MDN-0104举例说明了远程立体中心的非对映异构体配置分配中的困难和潜在的错误风险。但是，比较精细的13 C NMR偏差仍可为此类问题提供解决方案。
• LANTHIONINE DERIVATIVES
  申请人：Sato Seiichi

  公开号：US20120282386A1

  公开（公告）日：2012-11-08

  The present invention provides a variety of compounds having a CaSR agonist activity which possesses a superior kokumi-imparting function, and more particularly provides a kokumi-imparting composition, which contains the foregoing compound, and/or another substance having a CaSR agonist activity, in combination. The present invention also provides a kokumi-imparting composition which includes a lanthionine derivative and/or another substance having a CaSR agonist activity.

  本发明提供了一系列具有CaSR激动剂活性的化合物，具有优越的浓旨味作用，并更具体地提供了一种浓旨味作用的组合物，其中包含上述化合物和/或另一种具有CaSR激动剂活性的物质。本发明还提供了一种包含莰硫氨酸衍生物和/或另一种具有CaSR激动剂活性的物质的浓旨味作用组合物。
• Methods and intermediates for synthesizing SK1-I
  申请人：Enzo Biochem, Inc.

  公开号：US10364211B1

  公开（公告）日：2019-07-30

  The invention provides methods for synthesizing the compound (2R,3S,4E)-N-methyl-5-(4′-pentylphenyl)-2-aminopent-4-ene-1,3-diol, also known as SK1-I, and intermediate compounds used in its synthesis.

  该发明提供了合成化合物(2R,3S,4E)-N-甲基-5-(4'-戊基苯基)-2-氨基戊-4-烯-1,3-二醇，又称为SK1-I，以及用于其合成的中间化合物的方法。
• BICYCLIC COMPOUND AS RIP-1 KINASE INHIBITOR AND APPLICATION THEREOF
  申请人：Medshine Discovery Inc.

  公开号：EP3978492A1

  公开（公告）日：2022-04-06

  A compound represented by formula (I), isomers or pharmaceutically acceptable salts thereof, and application thereof in the preparation of drugs for treating diseases related to RIP-1 (receptor interacting protein) kinase.

  公式(I)所代表的化合物、同分异构体或其药学上可接受的盐，以及其在制备用于治疗与RIP-1（受体相互作用蛋白）激酶相关的疾病的药物中的应用。
• Deoxytrifluoromethylation of Alcohols
  作者：Nicholas E. Intermaggio、Agustin Millet、Dali L. Davis、David W. C. MacMillan

  DOI：10.1021/jacs.2c04807

  日期：2022.7.13

  Deoxy-functionalization of alcohols represents a class of reactions that has had a profound impact on modern medicine. In particular, deoxyfluorination is commonly employed as a means to incorporate high-value fluorine atoms into drug-like molecules. Recently, the trifluoromethyl (CF3) group has garnered attention from medicinal chemists due to its ability to markedly improve the pharmaceutical properties

  醇的脱氧功能化代表了一类对现代医学产生深远影响的反应。特别是，脱氧氟化作用通常用作将高价值氟原子掺入类药物分子中的一种手段。最近，三氟甲基 (CF 3 ) 基团因其能够显着改善小分子候选药物的药物特性而受到药物化学家的关注。然而，迄今为止，仍然没有实现类似的醇脱氧三氟甲基化的通用方法。我们在此报告了铜金属光氧化还原介导的直接脱氧三氟甲基化，其中醇底物被苯并恶唑盐原位激活，用于 C(sp 3 )–CF 3债券形成。