tert-butyl (R)-4-(2-hydroxypropan-2-yl)-2,2-dimethyloxazolidine-3-carboxylate | 288159-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: tert-butyl (R)-4-(2-hydroxypropan-2-yl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (4R)-4-(1-hydroxy-1-methyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylate；tert-Butyl (4R)-4-(1-hydroxy-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate；tert-butyl (4R)-4-(2-hydroxypropan-2-yl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 288159-36-4
• 化学式: C₁₃H₂₅NO₄
• 分子量: 259.346
• InChiKey: WRMSCAJFEZKYCB-SECBINFHSA-N

物化性质

• 熔点：
  36-37 °C
• 沸点：
  333.8±27.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-4-(2-hydroxypropan-2-yl)-2,2-dimethyloxazolidine-3-carboxylate 在 sodium chlorite 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 19.5h， 生成 (S)-(+)-2-氨基-3-羟基-3-甲基丁酸
  参考文献：
  名称：

  Gold-Catalyzed Amide/Carbamate-Linked N,O-Acetal Formation with Bulky Amides and Alcohols

  摘要：

  A gold-catalyzed N,O-acetal formation was established to construct an amide/carbamate-linked N,O-acetal substructure with bulky alcohols. The acyliminium cation species generated from o-alkynylbenzoic acid ester in the presence of a gold catalyst is highly reactive and underwent nucleophilic attack of various bulky alcohols and phenols at room temperature under neutral conditions, leading to the corresponding N,O-acetals in yields of 34-89% with good functional group tolerance.

  DOI：

  10.1021/acs.joc.0c02640
• 作为产物：
  描述：

  (2S)-(3,3-dimethyloxiran-2-yl)methanol 在 氢氧化钾 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 tert-butyl (R)-4-(2-hydroxypropan-2-yl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  The first simple and efficient synthesis of the unusual dipeptide part of Phomopsin A

  摘要：

  A practical high yielding synthesis of the key halogenated dipeptide part of Phomopsin A 2 is reported. The key steps are a selective Heck coupling, a Sharpless asymmetric dihydroxylation in PEG and a benzoyl isocyanate mediated synthesis of dehydrovaline. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.023

文献信息

• Radical‐Mediated Acyl Thiol‐Ene Reaction for Rapid Synthesis of Biomolecular Thioester Derivatives
  作者：Joshua T. McLean、Pierre Milbeo、Dylan M. Lynch、Lauren McSweeney、Eoin M. Scanlan

  DOI：10.1002/ejoc.202100615

  日期：2021.8.6

  Radical-mediated acyl thiol-ene reactions between biologically relevant alkene and thioacid components enables rapid, chemoselective and high yielding thioester formation. This reaction in combination with substrates that enable intramolecular acyl transfer permits access to native and modified products beyond the thioether linkage.

  生物相关烯烃和硫代酸组分之间自由基介导的酰基硫醇-烯反应能够快速、化学选择性和高产率地形成硫酯。该反应与能够进行分子内酰基转移的底物结合，允许获得超出硫醚键的天然和修饰产物。
• [EN] CYCLIZED SULFAMOYLARYLAMIDE DERIVATIVES AND THE USE THEREOF AS MEDICAMENTS FOR THE TREATMENT OF HEPATITIS B<br/>[FR] DÉRIVÉS DE SULFAMOYLARYLAMIDE CYCLISÉS ET LEUR UTILISATION À TITRE DE MÉDICAMENTS POUR LE TRAITEMENT DE L'HÉPATITE B
  申请人：JANSSEN SCIENCES IRELAND UC

  公开号：WO2017001655A1

  公开（公告）日：2017-01-05

  Inhibitors of HBV replication of Formula (I-A), including stereochemically isomeric forms, and salts, hydrates, solvates thereof, wherein Ra to Rd, and R1 to R8 have the meaning as defined herein. The present invention also relates to processes for preparing said compounds, pharmaceutical compositions containing them and their use, alone or in combination with other HBV inhibitors, in HBV therapy.

  乙肝病毒复制抑制剂公式(I-A)，包括立体化学异构体以及它们的盐、水合物、溶剂化物，其中Ra至Rd和R1至R8的含义如本文所述。本发明还涉及制备所述化合物的方法、含有它们的药物组合物以及它们单独使用或与其他乙肝病毒抑制剂结合在乙肝病毒治疗中的用途。
• [EN] N-1 BRANCHED ALKYL ETHER SUBSTITUTED IMIDAZO[4,5-C]QUINOLINE COMPOUNDS, COMPOSITIONS, AND METHODS<br/>[FR] COMPOSÉS IMIDAZO[4,5-C]QUINOLÉINE SUBSTITUÉS PAR ALKYLÉTHER N-1 RAMIFIÉ, COMPOSITIONS ET PROCÉDÉS
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2020109898A1

  公开（公告）日：2020-06-04

  Imidazo[4,5-c]quinoline compounds having a substituent that is attached at the N-1 position by a branched group, single enantiomers of the compounds, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed. Methods of use of the compounds as immune response modifiers, for inducing cytokine biosynthesis in humans and animals, and in the treatment of diseases including infectious and neoplastic diseases are also disclosed.

  本文披露了在N-1位置通过支链基团连接的取代基的咪唑并[4,5-c]喹啉化合物，化合物的单对映体，含有这些化合物的药物组合物，以及制备这些化合物的方法。还披露了作为免疫应答调节剂使用这些化合物的方法，用于诱导人类和动物中的细胞因子生物合成，并用于治疗包括传染性和肿瘤性疾病在内的疾病的方法。
• In Search of Small Molecules That Selectively Inhibit MBOAT4
  作者：Emily S. Murzinski、Ishika Saha、Hui Ding、David Strugatsky、Ryan A. Hollibaugh、Haixia Liu、Peter Tontonoz、Patrick G. Harran

  DOI：10.3390/molecules26247599

  日期：——

  Ghrelin is a 28-residue peptide hormone produced by stomach P/D1 cells located in oxyntic glands of the fundus mucosa. Post-translational octanoylation of its Ser-3 residue, catalyzed by MBOAT4 (aka ghrelin O-acyl transferase (GOAT)), is essential for the binding of the hormone to its receptor in target tissues. Physiological roles of acyl ghrelin include the regulation of food intake, growth hormone secretion from the pituitary, and inhibition of insulin secretion from the pancreas. Here, we describe a medicinal chemistry campaign that led to the identification of small lipopeptidomimetics that inhibit GOAT in vitro. These molecules compete directly for substrate binding. We further describe the synthesis of heterocyclic inhibitors that compete at the acyl coenzyme A binding site.

  胃饥饿素是由位于胃底粘膜的氧化腺中的P/D1细胞产生的一种由28个氨基酸残基组成的肽激素。通过MBOAT4（也称为胃饥饿素O-酰基转移酶（GOAT））催化其Ser-3残基的后转录辛酰化是该激素与靶组织中的受体结合所必需的。酰基饥饿素的生理作用包括调节食物摄入、促使垂体分泌生长激素以及抑制胰腺分泌胰岛素。在这里，我们描述了一项药物化学研究，该研究导致了对抑制体外GOAT的小型脂肽类似物的鉴定。这些分子直接竞争底物结合。我们进一步描述了在酰基辅酶A结合位点上竞争的杂环抑制剂的合成。
• Proof of the Existence of an Unstable Amino Acid: Pleurocybellaziridine in Pleurocybella porrigens
  作者：Toshiyuki Wakimoto、Tomohiro Asakawa、Saeko Akahoshi、Tomohiro Suzuki、Kaoru Nagai、Hirokazu Kawagishi、Toshiyuki Kan

  DOI：10.1002/anie.201004646

  日期：2011.2.1

  Angel's wing mushroom, Pleurocybella porrigens, caused fatal acute encephalopathy in Japan in 2004. The structures of cytotoxic amino acids previously isolated from the mushroom motivated a study to prove the existence of an aziridine amino acid, pleurocybellaziridine (1), found in the mushroom. The ester forms of synthetic 1 were used to confirm that the fruiting bodies contained high amounts of 1

  天使的翼形蘑菇菇菇（Pleurocybella porrigens）于2004年在日本引起了致命的急性脑病。先前从蘑菇中分离出的细胞毒性氨基酸的结构推动了一项研究，以证明在该蘑菇中发现了氮丙啶氨基酸（pleurocybellaziridine）（1）的存在。合成形式1的酯形式用于确认子实体中含有大量的1。此外，1对大鼠少突胶质细胞显示出明显的毒性。