(4S)-4-{[(benzyloxy)carbonyl]amino}-5-ethoxy-5-oxopentanoic acid | 5672-81-1

• 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: (4S)-4-{[(benzyloxy)carbonyl]amino}-5-ethoxy-5-oxopentanoic acid
• 英文别名: 1-ethyl N-(benzyloxycarbonyl)-L-glutamate；Z-Glu-OCH2CH3；α-ethyl N-benzyloxycarbonyl-L-glutamate；N-Cbz-L-Glutamic acid α-ethyl ester；N-benzyloxycarbonyl-L-glutamic acid α-ethyl ester；(S)-4-(((benzyloxy)carbonyl)amino)-5-ethoxy-5-oxopentanoic acid；N-Benzyloxycarbonyl-α-L-glutaminsaeure-ethylester；Benzyloxycarbonyl-L-glutaminsaeure-α-ethylester；N-Benzyloxycarbonyl-L-glutaminsaeure-monoethylester；N-Carbobenzoxy-L-glutaminsaeure-α-ethylester；N-Benzyloxycarbonyl-L-glutaminsaeure-1-aethylester；N-benzyloxycarbonyl-L-glutamic acid-1-ethyl ester；N-Benzyloxycarbonyl-L-glutaminsaeure-α-ethylester；(4S)-5-ethoxy-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 5672-81-1
• 化学式: C₁₅H₁₉NO₆
• 分子量: 309.319
• InChiKey: JNQYYJMIBOQAFC-LBPRGKRZSA-N

物化性质

• 熔点：
  88-89 °C
• 沸点：
  517.9±50.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-4-{[(benzyloxy)carbonyl]amino}-5-ethoxy-5-oxopentanoic acid 生成 (S)-2-aminopentanedioic acid 5-tert-butyl ester 1-ethyl ester
  参考文献：
  名称：

  脂族二硫化物的化学。十二。不对称开链胱氨酸衍生物的合成。

  摘要：

  DOI：

  10.1021/jo01277a025
• 作为产物：
  描述：

  L-谷氨酰胺 在 亚硝酸特丁酯 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 100.0h， 生成 (4S)-4-{[(benzyloxy)carbonyl]amino}-5-ethoxy-5-oxopentanoic acid
  参考文献：
  名称：

  WO2008/119032

  摘要：

  公开号：

文献信息

• Pyridyl-containing spirocyclic compounds as inhibitors of fibrinogen-dependent platelet aggregation
  申请人：——

  公开号：US20030055244A1

  公开（公告）日：2003-03-20

  Disclosed are certain substituted or unsubstituted pyridyl-containing spirocyclic compounds substituted with both basic and acidic functionality, which are useful in inhibiting platelet aggregation, inhibiting the binding of fibrinogen to blood platelets, and preventing or treating thrombosis

  本发明涉及某些含有取代或未取代吡啶基的螺环化合物，其取代有碱性和酸性功能，可用于抑制血小板聚集，抑制纤维蛋白原与血小板的结合，并预防或治疗血栓形成。
• Synthesis and Physicochemical Characterization of the Impurities of Pemetrexed Disodium, an Anticancer Drug
  作者：Olga Michalak、Mariusz Gruza、Anna Witkowska、Iwona Bujak、Piotr Cmoch

  DOI：10.3390/molecules200610004

  日期：——

  physicochemical characterization of the process-related impurities associated with the synthesis of pemetrexed disodium was performed. The possibility of pemetrexed impurities forming has been mentioned in literature, but no study on their structure has been published yet. This paper describes the development of the synthesis methods for these compounds and discusses their structure elucidation on the basis

  对与培美曲塞二钠合成相关的工艺相关杂质进行了物理化学表征。文献中已经提到形成培美曲塞杂质的可能性，但尚未发表对其结构的研究。本文描述了这些化合物的合成方法的发展，并讨论了基于二维 NMR 实验和 MS 数据的结构解析。这些杂质的鉴定应有助于培美曲塞二钠盐生产过程中的质量控制。
• <i>Bacillus subtilis</i>Esterase (BS2) and its Double Mutant Have Different Selectivity in the Removal of Carboxyl Protecting Groups
  作者：Efrosini Barbayianni、Christoforos G. Kokotos、Sebastian Bartsch、Christina Drakou、Uwe T. Bornscheuer、George Kokotos

  DOI：10.1002/adsc.200900325

  日期：2009.10

  An esterase from Bacillus subtilis (BS2) and its double mutant E188W/M193C quickly hydrolyze n-butyl, n-propyl, methoxyethyl and allyl esters. The wild-type BS2 preferentially removes such esters from the γ-position of glutamate diesters, while the engineered enzyme has a reversed selectivity removing esters from the α-position of glutamate diesters. Automated docking and molecular dynamic simulations

  从酯酶枯草芽孢杆菌（BS2）和它的双突变体E188W / M193C迅速水解Ñ丁基，Ñ丙基，甲氧基乙基和烯丙基酯。野生型BS2优先从谷氨酸二酯的γ-位除去这些酯，而工程酶具有相反的选择性，从谷氨酸二酯的α-位除去酯。进行了自动对接和分子动力学模拟，以了解不同区域选择性的分子原因。
• Synthesis of taxoids 5. Synthesis and evaluation of novel water-soluble prodrugs of a 3′-desphenyl-3′-cyclopropyl analogue of docetaxel
  作者：Tetsuo Yamaguchi、Naoyuki Harada、Kunihiko Ozaki、Hiroaki Arakawa、Kouji Oda、Noriyuki Nakanishi、Kenji Tsujihara、Tomiki Hashiyama

  DOI：10.1016/s0960-894x(99)00257-7

  日期：1999.6

  was synthesized from 10-deacetyl-baccatin III. The cytotoxicity of the new taxoid was evaluated against several human tumor cell lines, and it had ca. 20 times stronger activity against human colon cancer cell lines (WiDr and Colon 320) than that of docetaxel. This taxoid was converted to its water-soluble prodrugs that have 2'-substituted amino acid derivatives with spacer. The prodrugs had good solubility

  由10-脱乙酰基浆果赤霉素III合成了多西他赛的新型3'-去苯基-3'-环丙基类似物。评估了新的类紫杉醇对几种人类肿瘤细胞系的细胞毒性，并具有约。抗人结肠癌细胞系（WiDr和Colon 320）的活性是多西他赛的20倍。该紫杉烷被转化为其水溶性前药，其具有带有间隔基的2'-取代的氨基酸衍生物。该前药在盐水中具有良好的溶解性，并且比多西他赛对小鼠的B 16黑色素瘤具有更强的抗肿瘤活性。
• [EN] PRODUCTION PROCESSES OF S- AND O-DIACYLATED GAMMA-GLUTAMYL-CYSTEAMINE PRODRUGS<br/>[FR] PROCÉDÉS DE PRODUCTION DE PROMÉDICAMENTS DE GAMMA-GLUTAMYL-CYSTÉAMINE S-ET O-DIACYLÉS
  申请人：UNIV OF SUNDERLAND

  公开号：WO2020165601A1

  公开（公告）日：2020-08-20

  Methods are provided for the synthesis of a compound of formula (X). R2 is selected from -H, -C1-C4-alkyl,-C2-C4-alkenyl and C1-C4-aryl; R3 is selected from -C(O)H and -C(O)C1-C4-alkyl; and A is a pharmaceutically acceptable anion (e.g.a halide). Also provided are intermediate compounds formed during the synthesis.

  提供了一种合成化合物(X)的方法。其中，R2可选自-H、-C1-C4-烷基、-C2-C4-烯基和C1-C4-芳基；R3可选自-C(O)H和-C(O)C1-C4-烷基；A是药用可接受的阴离子（例如卤素）。同时提供了在合成过程中形成的中间化合物。