((S)-4-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexyl)-carbamic acid benzyl ester | 189188-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((S)-4-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexyl)-carbamic acid benzyl ester
• CAS: 189188-67-8
• 化学式: C₁₉H₂₆N₄O₅
• 分子量: 390.439
• InChiKey: DUTNMLHTDKTION-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  130.13
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((S)-4-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexyl)-carbamic acid benzyl ester 在 钯 盐酸 、 sodium hydroxide 、 氢气 、 silver(l) oxide 、 氯甲酸异丁酯 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Peptidyl β-homo-aspartals: Specific inhibitors of interleukin-1β converting enzyme and its homologues (caspases)

  摘要：

  Inhibition of interleukin-1 beta converting enzyme (ICE), apopain, papain, thrombin and trypsin with substrate like peptidyl L- and D-alpha-aldehydes and their L-beta-homo-aldehyde analogues was investigated. The L-beta-homo-aspartals appear to be specific inhibitors for ICE and its homologues; the other enzymes were not inhibited with such L-beta-homo aldehydes. Papain shows tolerance for D-residues at P-1 depending on their chiral stability. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00244-3
• 作为产物：
  描述：

  N-叔丁氧羰基-N'-苄氧羰基-L-鸟氨酸 以 三乙胺 为溶剂， 生成 ((S)-4-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Beta-amino acid derivatives as orally active non-peptide fibrinogen receptor antagonists

  摘要：

  The ornithine sulfonamide 1 was identified by random screening as weak fibrinogen receptor antagonist. Homologation of the carboxylic acid function and further structure activity studies led to the development of novel beta-amino acid derivatives, which are potent and orally active antagonists of the platelet fibrinogen receptor GPIIb/IIIa. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00095-4

文献信息

• Total synthesis of Myxoprincomide, a secondary metabolite from <i>Myxococcus xanthus</i>
  作者：Michael Kohr、Christine Walt、Jan Dastbaz、Rolf Müller、Uli Kazmaier

  DOI：10.1039/d2ob02021a

  日期：——

  Myxoprincomide, a secondary metabolite of the myxobacterium Myxococcus xanthus DK 1622, is synthesised for the first time. The central, unusual α-ketoamide is generated at the end of the synthesis to avoid side reactions during the synthesis of this rather reactive subunit. Nevertheless, the synthetic natural product is obtained as an isomeric mixture. Detailed analytical investigations show that the

  Myxoprincomide 是粘杆菌 Myxococcus xanthus DK 1622 的次级代谢产物，首次合成。中心的、不寻常的 α-酮酰胺是在合成结束时产生的，以避免在合成这种相当活泼的亚基过程中发生副反应。然而，合成天然产物是作为异构混合物获得的。详细的分析研究表明，在分离的天然产物中发现了相同的异构体混合物。
• Cycloadditions of Ketenes Generated in the Wolff Rearrangement. Stereoselective Synthesis of Aminoalkyl-Substituted β-Lactams from α-Amino Acids
  作者：Joachim Podlech、Michael R. Linder

  DOI：10.1021/jo9705069

  日期：1997.8.1

  Diazo ketones 1-16, derived from suitable protected amino acids (Ala, Leu, Val, Ile, Tie, Phe, Pro, Orn, Lys, Ser, and Thr), have been photochemically rearranged, leading to the corresponding ketene intermediates. They were trapped with N-benzylbenzaldimine 17 to give beta-lactams S-SS in up to 90% yield. In these cycloadditions, two of the four possible diastereoisomers were formed exclusively. The selectivity ranged from 60:40 to 93:7 and the bulkiness of the parent amino acid side chain is the governing factor. The relative configuration was-proved by three X-ray crystal structures. The diastereoselectivity in these reactions is also influenced by the use of chiral N-phenethylbenzaldimines 34 and 35. With regard to a projected deprotection of the lactam-nitrogen, N-allyl- (49) and N-(p-methoxybenzyl)benzaldimine (44) were used in this reaction. This led to the N-allyl beta-lactams 50 and 51 in 62 and 56% yield, respectively, and to the p-methoxybenzyl-substituted beta-lactams 45 and 46 (50 and 72% yield). The p-methoxybenzyl, group on the valine-derived beta-lactam 45a can be cleaved with potassium peroxodisulfate in 63% yield.