(S)-3-tert-Butoxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid benzyl ester | 84890-97-1

• 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)-3-tert-Butoxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid benzyl ester
• 英文别名: L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-anhydride with 2-methylpropyl hydrogen carbonate, 4-(phenylmethyl) ester；4-O-benzyl 1-O-(2-methylpropoxycarbonyl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioate
• CAS: 84890-97-1
• 化学式: C₂₁H₂₉NO₈
• 分子量: 423.463
• InChiKey: PZQBEIWRAISZHI-INIZCTEOSA-N

物化性质

• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  117.23
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-3-tert-Butoxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid benzyl ester 在 甲酸 、 苯甲醚 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  New Ion‐Exchange cum Separation Technique: A Study for the Synthesis of ω‐Guanidine containing Peptides using ω‐Amino Acid as Surrogate

  摘要：

  DOI：

  10.1080/00908320701230117
• 作为产物：
  描述：

  L-天冬氨酸-4-苄酯 在 N-甲基吗啉 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 (S)-3-tert-Butoxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid benzyl ester
  参考文献：
  名称：

  Synthesis of a peptidyldimannosyl phosphate: fragment of the variant-specific surface glycoprotein membrane anchor from trypanosoma brucei

  摘要：

  Condensation of protected beta-benzyl-aspartate 4 with 2-amino-ethanol, subsequent deprotection of the amino function and coupling with N',N'-di-benzylocarbonyl-lysine (7) afforded the peptidyl alcohol 8. Glycosylation of methyl 3,4,6 tri-O-benzyl-alpha-D-mannopyranoside (11) by ethyl 2,6-di-O-benzoyl-3,4-di-O-benzyl-1-thio-alpha-D-mannopyranoside (14) gave, after debenzoylation and protection of the 2'-hydroxyl function, the suitably protected dimannoside 21. Phosphitylation of 21 with benzyloxy-bis-(N, N-diisopropylamino)phosphine (18) followed by the addition of 8 gave, after oxidation and subsequent hydrogenolysis of the benzyl groups, the title compound in a good yield.

  DOI：

  10.1016/0040-4039(91)80242-x

文献信息

• Amino Acids and Peptides. XLVI. Introduction of Carboxyl Function into Pyrazinone by Using Newly Developed Procedure for Pyrazinone Ring Formation: Observation of Immediate Decarboxylation.
  作者：Hiroaki TAGUCHI、Toshio YOKOI、Yoshio OKADA

  DOI：10.1248/cpb.44.2037

  日期：——

  The carboxyl function was easily introduced into a pyrazinone ring by means of a newly developed procedure for pyrazinone ring formation from Asp- or Glu-containing dipeptidyl chloromethyl ketones : during the reaction, rapid decarboxylation from a carboxymethyl group at position 3 of 2(1H)-pyrazinone occurred due to the low electron density at position 3 of 2 (1H)-pyrazinone.

  通过一种新开发的从含有天冬氨酸或谷氨酸的二肽氯甲基酮形成吡嗪酮环的方法，可以很容易地将羧基功能引入吡嗪酮环：在反应过程中，由于2(1H)-吡嗪酮的第3位电子密度较低，从第3位的羧甲基快速脱羧发生在2(1H)-吡嗪酮上。
• A facile synthesis of chiral N-protected β-amino alcohols.
  作者：Marc Rodriguez、Muriel Llinares、Sylvie Doulut、Annie Heitz、Jean Martinez

  DOI：10.1016/s0040-4039(00)92121-x

  日期：1991.2

  Chiral N-protected β-amino alcohols are easily obtained by NaBH4 reduction of mixed anhydrides of N-protected α-amino acids in an organic/aqueous medium. The alcohols obtained from side chain or main chain reduction of N-protected aspartic acid are converted in good yields into lactones.

  通过在有机/水介质中通过NaBH 4还原N-保护的α-氨基酸的混合酸酐可以容易地获得手性的N-保护的β-氨基醇。由N-保护的天冬氨酸的侧链或主链还原得到的醇以良好的产率转化为内酯。
• Discovery, Synthesis, and Biological Evaluation of a Novel Group of Selective Inhibitors of Filoviral Entry
  作者：Maria V. Yermolina、Jizhen Wang、Michael Caffrey、Lijun L. Rong、Duncan J. Wardrop

  DOI：10.1021/jm1008715

  日期：2011.2.10

  Herein, we report the development of an antifiloviral screening system, based on a pseudotyping strategy, and its application in the discovery of a novel group of small molecules that selectively inhibit the Ebola and Marburg glycoprotein (GP)-mediated infection of human cells. Using Ebola Zaire GP-pseudotyped HIV particles bearing a luciferase reporter gene and 293T cells, a library of 237 small molecules

  在此，我们报告了基于假型策略的抗丝病毒筛选系统的开发，及其在发现一组新的小分子中的应用，这些小分子选择性地抑制了埃博拉病毒和马尔堡糖蛋白 (GP) 介导的人类细胞感染。使用带有荧光素酶报告基因和 293T 细胞的 Ebola Zaire GP 假型 HIV 颗粒，筛选了 237 个小分子库以抑制 GP 介导的病毒进入。从该测定中，先导化合物8a被鉴定为丝状病毒进入的选择性抑制剂，IC 5030 μM。为了分析功效的官能团要求，然后使用“点击”化学制备的 56 种异恶唑和三唑衍生物对这种 3,5-二取代异恶唑进行结构-活性关系分析。该研究表明，虽然异恶唑环可以被三唑系统取代，但在8a 中发现的 5-（二乙氨基）乙酰胺取代基是抑制病毒细胞进入所必需的。3-芳基取代基的变化提供了许多更有效的抗病毒剂，IC 50值范围为2.5 μM。还发现先导化合物8a及其三种衍生物可阻断马尔堡糖蛋白 (GP) 介导的人类细胞感染。
• Amino Acids and Peptides. XX. Preparation of .BETA.-Cyclododecyl Aspartate and Its Application to Synthesis of Fibronectin- and Laminin-Related Peptides.
  作者：Koichi KAWASAKI、Tomohiro MURAKAMI、Kazuyoshi KOSHINO、Machiko NAMIKAWA、Mitsuko MAEDA、Takao HAMA、Tadanori MAYUMI

  DOI：10.1248/cpb.42.792

  日期：——

  beta-Cyclododecyl aspartate was prepared and its application to peptide synthesis was examined. Derivatives of beta-cyclododecyl aspartate are more likely to crystallize and should be useful for peptide synthesis. The cyclododecyl ester was much stable to bases than the benzyl ester and rather more stable than the cyclohexyl ester. It was removable by HF treatment and trifluoromethanesulfonic acid treatment

  制备了β-环十二烷基天冬氨酸盐，并研究了其在肽合成中的应用。β-环十二烷基天冬氨酸的衍生物更容易结晶，应该对肽合成有用。环十二烷基酯对碱的稳定性比苄基酯高，但比环己基酯更稳定。可通过HF处理和三氟甲磺酸处理将其除去。β-环十二烷基天冬氨酸盐通过固相和液相方法用于合成层粘连蛋白和纤连蛋白相关肽。
• Synthesis and Biological Activity of Novel L-Amino Acid Based Analgesic Compounds
  作者：Junzhu Pan、Qianqian Wang、Gu He、Liang Ouyang、Li Guo

  DOI：10.2174/157018010791163497

  日期：2010.6.1

  Synthesis and analgesic activity studies of a series of L-amino acid based compounds were described. These compounds were designed as potential N-type Calcium Channel Blockers and their structures were confirmed by 1H NMR and ESI-MS spectra. Some of the compounds exhibited significant analgesic activity in Mouse Hot-Plate tests. According to the data of pharmacological experiments, we carried out preliminary

  描述了一系列基于L-氨基酸的化合物的合成和镇痛活性。这些化合物被设计为潜在的N型钙通道阻滞剂，其结构通过1H NMR和ESI-MS光谱确认。某些化合物在Mouse Hot-Plate测试中显示出明显的镇痛活性。根据药理实验数据，我们进行了初步的结构活性研究，结果表明这种化合物可用于开发新的止痛药。