α-tert-Butyl β-S-ethyl (S)-N-(tert-butoxycarbonyl)thioaspartate | 147698-03-1

• 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: α-tert-Butyl β-S-ethyl (S)-N-(tert-butoxycarbonyl)thioaspartate
• 英文别名: tert-butyl (2S)-4-ethylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
• CAS: 147698-03-1
• 化学式: C₁₅H₂₇NO₅S
• 分子量: 333.449
• InChiKey: QXGLFLQCLBBGMV-JTQLQIEISA-N

物化性质

• 沸点：
  437.3±40.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α-tert-Butyl β-S-ethyl (S)-N-(tert-butoxycarbonyl)thioaspartate 在 三乙基硅烷 、 palladium 10% on activated carbon 、 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 15.08h， 生成 (S)-tert-butyl-4-((2-(1H-indol-3-yl)ethyl)(((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)amino)-2-((tert-butoxycarbonyl) amino)butanoate
  参考文献：
  名称：

  Development of rationally designed DNA N6 adenine methyltransferase inhibitors

  摘要：

  A series of bisubstrate inhibitors for DNA N6 adenine methyltransferase (Dam) have been synthesized by linking an amine analogue of S-adenosylmethionine to an aryl moiety designed to probe the binding pocket of the DNA adenine base. An initial structure-activity relationship study has identified substituents that increase inhibitor potency to the similar to 10 mu M range and improve selectivity against the human cytosine methyltransferase Dnmt1. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.072
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 41.0h， 生成 α-tert-Butyl β-S-ethyl (S)-N-(tert-butoxycarbonyl)thioaspartate
  参考文献：
  名称：

  Chirospecific synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane, precursor for carbocyclic nucleoside synthesis. Dieckmann cyclization with an .alpha.-amino acid

  摘要：

  Carbocyclic nucleosides are important isosteres of nucleosides possessing a variety of antiviral and antineoplastic activities. We report here a new method for the chirospecific synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane. This compound is a key precursor for the synthesis of some carbocyclic nucleosides. The method involves (1) an improved synthesis of (S)-2-aminoadipic acid; (2) Dieckmann cyclization of this alpha-amino acid to an aminocyclopentanone; and (3) elaboration of the latter to the target (1S,3R)-l-amino-3-(hydroxymethyl)cyclopentane. The starting (S)-2-aminoadipic acid delta-methyl ester was prepared enantiomerically pure from (S)-aspartic acid in 51% overall yield. Dieckmann condensation converted this amino acid to a (methoxycarbonyl)-cyclopentanone, and reduction of the ketone followed by elimination yielded (S)-3-[N-(9-phenylfluoren-9-yl)amino]-1-(methoxycarbonyl)cyclopentene. Reduction of the double bond gave a mixture of the cis and trans diastereomers. This mixture was converted to a single diastereomer by epimerization and trapping of the cis isomer as (1S,4R)-2-(9-phenylfluoren-9-yl)-2-azabicyclo[2.2.1]heptan-3-one. Hydrolytic cleavage of the lactam followed by reduction gave (IS,3R)-1-amino-3-(hydroxymethyl)-cyclopentane.

  DOI：

  10.1021/jo00061a006

文献信息

• [EN] BROAD SPECTRUM ANTI-CANCER COMPOUNDS<br/>[FR] COMPOSÉS ANTICANCÉREUX À LARGE SPECTRE
  申请人：UNIV CALIFORNIA

  公开号：WO2021076617A1

  公开（公告）日：2021-04-22

  Described herein, inter alia, are compounds for treating cancer and methods of use. This disclosure features chemical entities (e.g., small hairpin RNAs (shRNAs), micro RNA (miRNAs), small interfering RNA (siRNAs), small molecule inhibitors, antisense nucleic acids, peptides, viruses, CRISPR-sgRNAs, or combinations thereof) that inhibit one or more of m6A writers (e.g., methyltransferase like 3 (Mettl3 or MT-A70) or methyltransferase like-14 (Mettl14)), m6Am writers (e.g., phosphorylated CTD interacting factor I (PCIF 1), or Mettl3/14), m6A erasers (e.g., fat-mass and obesity-associated protein (FTO) or ALKB homolog 5 (ALKBH5)), m6Am erasers (e.g., FTO), m6A readers (e.g., YTH domain-containing family proteins (YTHs)), YTF domain family member 1 (YTHDF 1), YTF domain family member 2 (YTHDF 2), YTF domain family member 3 (YTHDF 3), or tyrosine-protein phosphatase non-receptor type 2 (PTPN2).

  本文描述了用于治疗癌症的化合物和使用方法。该公开涉及抑制m6A编写酶（例如，甲基转移酶类3（Mettl3或MT-A70）或甲基转移酶类14（Mettl14））、m6Am编写酶（例如，磷酸化CTD相互作用因子I（PCIF 1）或Mettl3/14）、m6A擦除酶（例如，脂肪质量和肥胖相关蛋白（FTO）或ALKB同源物5（ALKBH5））、m6Am擦除酶（例如，FTO）、m6A读取器（例如，YTH结构域含家族蛋白（YTHs））、YTF结构域家族成员1（YTHDF 1）、YTF结构域家族成员2（YTHDF 2）、YTF结构域家族成员3（YTHDF 3）或酪氨酸蛋白磷酸酶非受体型2（PTPN2）等化学实体（例如，小发夹RNA（shRNAs）、微RNA（miRNAs）、小干扰RNA（siRNAs）、小分子抑制剂、反义核酸、肽、病毒、CRISPR-sgRNAs或其组合）。
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  作者：Kalyan Kumar Pasunooti、Renliang Yang、Seenuvasan Vedachalam、Bala Kishan Gorityala、Chuan-Fa Liu、Xue-Wei Liu

  DOI：10.1016/j.bmcl.2009.09.107

  日期：2009.11

  A general and diastereoselective synthesis of (2S, 4S)-4-mercapto-l-lysine derivative was described. The key features of this synthesis include Zn-mediated diastereoselective Reformatsky reaction and selective reduction of methyl ester with sodium borohydride. Introduction of thiol functional group on lysine side chain proved to be appropriate for dual native chemical ligation. This methodology allows

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  DOI：10.1016/s0960-894x(02)00923-x

  日期：2003.1

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• Synthesis of an Azido Precursor to (2<i>S</i>,5<i>R</i>)-5-Hydroxylysine Using an Asymmetric Organocatalytic Chlorination/Reduction Sequence
  作者：Manuel Johannes、Margaret A. Brimble

  DOI：10.1021/jo402220s

  日期：2013.12.20

  An efficient, robust, and scalable synthesis of an azido precursor to the modified amino acid (2S,5R)-5-hydroxylysine was developed on the basis of the use of a highly stereoselective organocatalytic alpha-chlorination-reduction protocol. The final Fmoc-protected (2S,5R)-6-azido-5-hydroxylysine derivative can be used in solid-phase peptide synthesis, providing access to proteins that contain large quantities of post-translationally modified lysine (e.g., collagens).