N-(tert-butyloxycarbonyl)-trans-(1S,2S)-2-aminocyclopentanecarboxylic acid methyl ester | 192385-82-3

• 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: N-(tert-butyloxycarbonyl)-trans-(1S,2S)-2-aminocyclopentanecarboxylic acid methyl ester
• 英文别名: (1S,2S)-(+)-methyl 2-(tert-butoxycarbonylamino)cyclopentanecarboxylate；methyl (1S,2S)-2-(tert-butoxycarbonylamino)cyclopentanecarboxylate；methyl (1S,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylate
• CAS: 192385-82-3
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: LVSNFSRSQZFNPY-IUCAKERBSA-N

物化性质

• 熔点：
  66-67 °C
• 沸点：
  331.8±31.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(tert-butyloxycarbonyl)-trans-(1S,2S)-2-aminocyclopentanecarboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 (1S,2s)-boc-2-氨基环戊烷羧酸
  参考文献：
  名称：

  Synthesis of enantiomerically pure cis and trans 2-aminocyclopentanecarboxylic acids. Use of proline replacements in potential HIV-protease inhibitors

  摘要：

  The synthesis of the four diastereomeric 2-aminocyclopentanecarboxylic acids, their use as replacements for proline in potential HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere and the evaluation of the biological activity of these is described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00482-1
• 作为产物：
  描述：

  methyl (3R)-3-[(benzyloxy)carbonylamino]-5-methylsulfanylpentanoate 在 Grubbs catalyst first generation 、 双氧水 、 碳酸氢钠 、 溶剂黄146 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 间二甲苯 、 苯 为溶剂， 反应 55.0h， 生成 N-(tert-butyloxycarbonyl)-trans-(1S,2S)-2-aminocyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Cyclic β-Amino Acid Esters from Methionine, Allylglycine, and Serine

  摘要：

  Here we report a versatile ring-closing metathesis-based approach to 5-, 6-, and 7-membered cyclic beta-amino esters starting with simple and readily available building blocks-methionine, allylglycine, and serine-where the nature of the amino acid determines the size of the carbocyclic ring.

  DOI：

  10.1021/jo049794g

文献信息

• Radical cyclization in heterocycle synthesis. Part 13: Sulfanyl radical addition–cyclization of oxime ethers and hydrazones connected with alkenes for synthesis of cyclic β-amino acids
  作者：Okiko Miyata、Kanami Muroya、Tomoko Kobayashi、Rina Yamanaka、Seiko Kajisa、Junko Koide、Takeaki Naito

  DOI：10.1016/s0040-4020(02)00412-x

  日期：2002.5

  combination of sulfanyl radical addition–cyclization of the oxime ethers and hydrazones connected with alkenes and subsequent conversion of a phenylsulfanylmethyl group to a carboxyl group provides a novel method for the construction of the cyclic β-amino acids. Upon treatment with thiophenol in the presence of AIBN, the oxime ethers and hydrazones smoothly underwent sulfanyl radical addition-cyclization

  硫醚基自由基加成－肟醚和与烯烃连接的的环化反应以及随后苯硫烷基甲基到羧基的转化提供了一种构造环状β-氨基酸的新方法。在AIBN存在下用苯硫酚处理后，使肟醚和平稳地进行硫烷基自由基加成-环化反应，得到2-（苯基硫烷基甲基）环烷基胺。该方法已成功应用于2-氨基环戊烷羧酸和4-氨基-3-吡咯烷羧酸的实际合成。
• PENTACYCLIC COMPOUND
  申请人：Eisai R&D Management Co., Ltd.

  公开号：US20190071452A1

  公开（公告）日：2019-03-07

  The present invention provides compounds represented by formulas (I) to (VI) or pharmaceutically acceptable salts thereof.

  本发明提供由化学式（I）至（VI）表示的化合物或其药用可接受的盐。
• Nucleophilic openings of bicyclic β-lactones via acyl C–O and alkyl C–O cleavage: catalytic, asymmetric synthesis of a versatile, carbocyclic nucleoside precursor and protected transpentacin
  作者：Yasuno Yokota、Guillermo S Cortez、Daniel Romo

  DOI：10.1016/s0040-4020(02)00703-2

  日期：2002.8

  recently developed in our laboratory. These bicyclic β-lactones undergo facile ring cleavage under mild conditions via both acyl C–O and alkyl C–O bond cleavage. Cleavage of the acyl C–O bond with hydroxylamine nucleophiles proceeds at ambient temperature and reductive cleavage is readily accomplished with aluminum and boron reducing agents. Alternatively, alkyl C–O cleavage with various nucleophiles leads

  通过我们实验室最近开发的分子内催化，不对称亲核试剂催化的醛醇内酯化反应，可得到多种与碳环融合的β-内酯。这些双环β-内酯在温和条件下会通过酰基C-O和烷基C-O键断裂而容易地断裂。酰基C–O键与羟胺亲核试剂的裂解在环境温度下进行，而还原性裂解可通过铝和硼还原剂轻松完成。另外，用各种亲核试剂进行的烷基C-O裂解会导致多种反式-β-取代的环戊烷羧酸。这些转化的效用通过保护的（1 S，2 S）-反戊酸和通用二醇，用于碳环核苷的合成。
• Versatile Post‐synthetic Modifications of Helical β‐Peptide Foldamers Derived from a Thioether‐Containing Cyclic β‐Amino Acid
  作者：Danim Lim、Wonchul Lee、Jungwoo Hong、Jintaek Gong、Jonghoon Choi、Jaewook Kim、Seolhee Lim、Sung Hyun Yoo、Yunho Lee、Hee‐Seung Lee

  DOI：10.1002/anie.202305196

  日期：2023.9.25

  We introduce a novel cyclic β‐amino acid, trans‐(3S,4R)‐4‐aminotetrahydrothiophene‐3‐carboxylic acid (ATTC), as a versatile building block for designing peptide foldamers with controlled secondary structures. We synthesized and characterized a series of β‐peptide hexamers containing ATTC using various techniques, including X‐ray crystallography, circular dichroism, and NMR spectroscopy. Our findings reveal that ATTC‐containing foldamers can adopt 12‐helical conformations similar to their isosteres and offer the possibility of fine‐tuning their properties via post‐synthetic modifications. In particular, chemoselective conjugation strategies demonstrate that ATTC provides unique post‐synthetic modification opportunities, which expand their potential applications across diverse research areas. Collectively, our study highlights the versatility and utility of ATTC as an alternative to previously reported cyclic β‐amino acid building blocks in both structural and functional aspects, paving the way for future research in the realm of peptide foldamers and beyond.

  摘要 我们介绍了一种新型环状β-氨基酸--反式-(3S,4R)-4-氨基四氢噻吩-3-羧酸（ATTC），它是设计具有可控二级结构的肽折叠体的多功能构建模块。我们利用 X 射线晶体学、圆二色光谱和核磁共振光谱等多种技术合成了一系列含有 ATTC 的 β 肽六聚体，并对其进行了表征。我们的研究结果表明，含有 ATTC 的折叠体可以采用与其同源物类似的 12 螺旋构象，并提供了通过合成后修饰微调其特性的可能性。特别是化学选择性共轭策略表明，ATTC 提供了独特的合成后修饰机会，从而拓展了它们在不同研究领域的潜在应用。总之，我们的研究强调了 ATTC 作为以前报道过的环状 β- 氨基酸构筑基块的替代品在结构和功能方面的多功能性和实用性，为肽折叠器领域及其他领域的未来研究铺平了道路。
• Asymmetric Synthesis of <i>anti</i>-α-Substituted β-Amino Ketones from Sulfinimines
  作者：Franklin A. Davis、Peng Xu

  DOI：10.1021/jo2002352

  日期：2011.5.6

  Previously unknown, enantiopure, beta-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-alpha-substituted beta-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-alpha-substituted isomers which did. The anti-alpha-substituted beta-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-alpha-substituted beta-amino esters because alpha-alkylation of N-sulfinyl beta-amino Weinreb amide enolates resulted in poor diastereoselectivities.