(S)-tert-butyl 2,6-dimethyl-3-oxohept-1-en-4-ylcarbamate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-tert-butyl 2,6-dimethyl-3-oxohept-1-en-4-ylcarbamate
• 英文别名: tert-butyl N-(2,6-dimethyl-3-oxohept-1-en-4-yl)carbamate
• 化学式: C₂₀H₃₈N₃O₅Pol
• 分子量: 255.35
• InChiKey: BRMIWZWAGRRHEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 2,6-dimethyl-3-oxohept-1-en-4-ylcarbamate 在 1,1,1-三氟丙酮 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 以38%的产率得到N-[(2S)-4-甲基-1-[(2R)-2-甲基环氧乙烷-2-基]-1-氧代-2-戊基]氨基甲酸叔丁酯
  参考文献：
  名称：

  O-GlcNAc Peptide Epoxyketones Are Recognized by Mammalian Proteasomes

  摘要：

  Cytosolic and nuclear proteins may be subject to both O-GlcNAcylation and proteasomal degradation. By means of activity-based profiling, we demonstrate that O-GlcNAc serine-containing peptide epoxyketones bind to the proteasome catalytic active sites and thus provide the first clear evidence that proteasomes recognize peptides post-translationally modified with a GlcNAc moiety.

  DOI：

  10.1021/ja901231w
• 作为产物：
  描述：

  5-[4-Fluoro-2-[[1-[2-oxo-2-(4-pentylanilino)ethyl]triazol-4-yl]methoxy]phenyl]-1,2-oxazole-3-carboxylic acid 在 哌啶 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 (S)-tert-butyl 2,6-dimethyl-3-oxohept-1-en-4-ylcarbamate
  参考文献：
  名称：

  O-GlcNAc Peptide Epoxyketones Are Recognized by Mammalian Proteasomes

  摘要：

  Cytosolic and nuclear proteins may be subject to both O-GlcNAcylation and proteasomal degradation. By means of activity-based profiling, we demonstrate that O-GlcNAc serine-containing peptide epoxyketones bind to the proteasome catalytic active sites and thus provide the first clear evidence that proteasomes recognize peptides post-translationally modified with a GlcNAc moiety.

  DOI：

  10.1021/ja901231w

文献信息

• [EN] PROCESS FOR THE PREPARATION OF (2S)-N-((S)-1-((S)-4-METHYL-1-((R)-2-METHYL OXIRAN-2-YL)-1-OXOPENTAN-2-YLCARBAMOYL)-2-PHENYLETHYL)-2-((S)-2-(2-MORPHOLINO ACETAMIDO)-4-PHENYLBUTANAMIDO)-4-METHYLPENTANAMIDE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE (2S)-N-((S)-1-((S)-4-MÉTHYL-1-((R)-2-MÉTHYL OXIRAN-2-YL)-1-OXOPENTAN-2-YLCARBAMOYL)-2-PHÉNYLÉTHYL)-2-((S)-2-(2-MORPHOLINO ACÉTAMIDO)-4-PHÉNYLBUTANAMIDO)-4-MÉTHYLPENTANAMIDE
  申请人：MSN LABORATORIES PRIVATE LTD

  公开号：WO2016170544A1

  公开（公告）日：2016-10-27

  The present invention relates to process for the preparation of (2S)-N-((S)-l -((S)-4-methyl-1 -((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylcarbamoyl)-2-phenylethyl)-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)-4 -methylpentanamide represented by the following structural formula-1.

  本发明涉及一种制备(2S)-N-((S)-l -((S)-4-甲基-1-((R)-2-甲氧基环氧丙基-1-氧代戊基氨基)-2-苯乙基)-2-((S)-2-(2-吗啉基乙酰氨基)-4-苯基丁酰氨基)-4-甲基戊酰胺的方法，其结构式如下所示-1。
• Crystalline peptide epoxy ketone protease inhibitors and the synthesis of amino acid keto-epoxides
  申请人：Phiasivongsa Pasit

  公开号：US20090105156A1

  公开（公告）日：2009-04-23

  The invention relates to crystalline peptide keto epoxide compounds, methods of their preparation, and related pharmaceutical compositions. This invention also relates to methods for the preparation of amino acid keto-epoxides. Specifically, allylic ketones are stereoselectively converted to the desired keto epoxides.

  这项发明涉及结晶肽酮环氧化合物、其制备方法以及相关的药物组合物。该发明还涉及氨基酸酮环氧化合物的制备方法。具体来说，烯丙基酮被立体选择性地转化为所需的酮环氧化合物。
• [EN] SYNTHESIS OF (S)-2-AMINO-4-METHYL-1-((R)-2-METHYLOXIRANE-2-YL)-PENTAN-1-ONE AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF<br/>[FR] SYNTHÈSE DE (S)-2-AMINO-4-MÉTHYL-1-((R)-2-MÉTHYLOXIRANE-2-YL)-PENTAN-1-ONE ET DE SES SELS PHARMACEUTIQUEMENT ACCEPTABLES
  申请人：AMGEN INC

  公开号：WO2018027021A1

  公开（公告）日：2018-02-08

  The present invention provides new methods for preparing compound (5), and pharmaceutically acceptable salts thereof, of structure. Compound (5), or a pharmaceutically acceptable salt thereof, is an important intermediate in the synthesis of carfilzomib. The invention further provides methods of making a useful manganese catalyst that may be used in the epoxidation step of the present invention.

  本发明提供了制备化合物(5)及其药学上可接受的盐的新方法，该化合物具有特定结构。化合物(5)或其药学上可接受的盐是合成卡非佐米的重要中间体。本发明还提供了制备一种有用的锰催化剂的方法，该催化剂可用于本发明中的环氧化步骤。
• [EN] AN IMPROVED PROCESSES FOR THE PREPARATION OF CARFILZOMIB OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF<br/>[FR] PROCÉDÉ PERFECTIONNÉ DE PRÉPARATION DE CARFILZOMIB OU DE SELS PHARMACEUTIQUEMENT ACCEPTABLES DE CELUI-CI
  申请人：LAURUS LABS PRIVATE LTD

  公开号：WO2016185450A1

  公开（公告）日：2016-11-24

  The present invention relates to an improved process for the preparation of carfilzomib or a pharmaceutically acceptable salt thereof. The present invention also relates to a process for the preparation of amorphous form of carfilzomib.

  本发明涉及一种改进的制备卡菲唑胺或其药学上可接受的盐的工艺。本发明还涉及一种制备卡菲唑胺非晶态形式的工艺。
• [EN] CRYSTALLINE PEPTIDE EPOXY KETONE PROTEASE INHIBITORS AND THE SYNTHESIS OF AMINO ACID KETO-EPOXIDES<br/>[FR] INHIBITEURS DE PROTÉASE ÉPOXY-CÉTONE PEPTIDIQUE CRISTALLINE, ET SYNTHÈSE DE CÉTO-ÉPOXYDES D'ACIDES AMINÉS
  申请人：PROTEOLIX INC

  公开号：WO2009045497A1

  公开（公告）日：2009-04-09

  The invention relates to crystalline peptide keto epoxide compounds, methods of their preparation, and related pharmaceutical compositions. This invention also relates to methods for the preparation of amino acid keto-epoxides. Specifically, allylic ketones are stereoselectively converted to the desired keto epoxides.

  本发明涉及晶体肽酮环氧化合物的制备方法以及相关的制药组合物。本发明还涉及氨基酸酮环氧化物的制备方法。具体地，烯丙基酮被立体选择性地转化为所需的酮环氧化物。