N,N'-Dicarbobenzoxy-L-β-lysin | 35107-12-1

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: N,N'-Dicarbobenzoxy-L-β-lysin
• 英文别名: (3S)-3,6-Bis{[(benzyloxy)carbonyl]amino}hexanoic acid；(3S)-3,6-bis(phenylmethoxycarbonylamino)hexanoic acid
• CAS: 35107-12-1
• 化学式: C₂₂H₂₆N₂O₆
• 分子量: 414.458
• InChiKey: LHJJHUUMPVVEBX-IBGZPJMESA-N

物化性质

• 沸点：
  662.7±55.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-Dicarbobenzoxy-L-β-lysin 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 35.0 ℃ 、101.32 kPa 条件下， 反应 6.0h， 以100%的产率得到β-lysine
  参考文献：
  名称：

  Keirs, David; Moffat, David; Overton, Karl, Journal of the Chemical Society. Perkin transactions I, 1991, # 5, p. 1041 - 1051

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N'-双[苄氧羰基]-L-鸟氨酸 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 N,N'-Dicarbobenzoxy-L-β-lysin
  参考文献：
  名称：

  Synthesis of Acyl Derivatives of β-Lysine for Peptide Synthesis

  摘要：

  通过混合碳羧酸酐制备重氮酮的改良 Arndt-Eistert 反应，从相应的二酰-l-鸟氨酸合成了二苄氧羰基-和二叔丁氧羰基-l-β-赖氨酸。这些二酰-β-赖氨酸衍生物是全合成或半合成多肽抗生素、结核菌素或链霉素所必需的。

  DOI：

  10.1246/bcsj.48.2401

文献信息

• Tan-1057 derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US06617332B1

  公开（公告）日：2003-09-09

  The invention relates to novel natural product derivatives of the formula (I), to processes for their preparation, to pharmaceutical compositions comprising them and to their use in the treatment of disorders in humans or animals: in which R1, D, X, Y and Z are defined as in claim 1.

  该发明涉及公式（I）的新型天然产物衍生物，以及其制备过程、包含它们的药物组合物以及它们在治疗人类或动物疾病中的应用：其中R1、D、X、Y和Z的定义如权利要求1中所述。
• The convergent total synthesis and antibacterial profile of the natural product streptothricin F
  作者：Matthew G. Dowgiallo、Brandon C. Miller、Mintesinot Kassu、Kenneth P. Smith、Andrew D. Fetigan、Jason J. Guo、James E. Kirby、Roman Manetsch

  DOI：10.1039/d1sc06445b

  日期：——

  The second ever total synthesis of streptothricin F and the first achieved through a diversity-enabling convergent route. The synthesis is achieved in 35 total steps, with a longest linear sequence of 19 steps, and 0.40% overall yield.

  第二次合成链霉素F的全合成，首次通过多样性促进的汇聚路线实现。该合成共经过35个步骤，最长线性序列为19步，总产率为0.40%。
• Syntheses and properties of negamycin analogs modified the .DELTA.-hydroxy-.BETA.-lysine moiety.
  作者：SHINICHI KONDO、KATSUHARU IINUMA、KENZABURO YOSHIDA、KAZUTERU YOKOSE、YOKO IKEDA、MASAMI SHIMAZAKI、HAMAO UMEZAWA

  DOI：10.7164/antibiotics.29.208

  日期：——
• Taniyama,H. et al., Chemical and pharmaceutical bulletin, 1972, vol. 20, p. 601 - 604
  作者：Taniyama,H. et al.

  DOI：——

  日期：——
• First enantioselective synthesis of the novel antiinfective TAN-1057A via its aminomethyl-substituted dihydropyrimidinone heterocycle
  作者：Vladimir N. Belov、Michael Brands、Siegfried Raddatz、Jochen Krüger、Sofia Nikolskaya、Viktor Sokolov、Armin de Meijere

  DOI：10.1016/j.tet.2004.06.034

  日期：2004.8

  Enantiomerically pure N-2-Z-N-2-MeAsnOH [(S)-14], prepared in 8 steps (23% overall yield) from asparaginic acid, was first subjected to a Hofmann degradation with PhI(OCOCF3)(2) yielding (S)-N-2-Z-N-2-methyl-2,3-diaminopropanoic acid [N-2-Z-N-2-Me-L-A(2)pr, (S)-15], and this in turn was protected to give N-2-Z-N-3-Boc-N-2-Me-L-A(2)pr [(S)-17]. Condensation of (S)-17 with HN=C(SMe)NHCONH2 followed by removal of the tert-butoxycarbonyl protecting group, cyclization and hydrogenolytic removal of the Z-group gave the heterocycle of TAN-1057A [(S)-1] with an e.e. of 87 in 36% yield [from (S)-14]. Coupling of (S)-1 with (S)-tris-Z-beta-homoarginine (20a) in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) and iPr(2)NEt in N,N-dimethyl-acetamide followed by hydrogenolysis afforded the most active A-diastereomer of the natural antibiotic TAN-1057 in 52% yield (from (S)-1 and 20a). Similarly, starting from (S)-1, a single diastereomer of the potent, less toxic TAN-1057A analogue 22b with a beta-lysine side chain has been prepared. All described synthetic steps do not require column chromatography for purification of the products. (C) 2004 Elsevier Ltd. All rights reserved.