allo-1-(4-tolylsulfonyl)-4-<<(4-methylphenyl)sulfonyl>oxy>-D-proline ethyl ester | 116143-05-6

• 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: allo-1-(4-tolylsulfonyl)-4-<<(4-methylphenyl)sulfonyl>oxy>-D-proline ethyl ester
• 英文别名: allo-1-(4-Tolylsulfonyl)-4-((4-tolylsulfonyl)oxy)-D-proline Ethyl Ester；Ethyl (2R,4R)-N-Tosyl-4-tosyloxy-2-pyrrolidinecarboxylate；(4R)-[(4-methylphenyl)sulfonyl]-4-[[(4-methylphenyl)sulfonyl]oxy]-D-proline ethyl ester；(2R,4R)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic acid ethyl ester；ethyl (2R,4R)-1-(4-methylphenyl)sulfonyl-4-(4-methylphenyl)sulfonyloxypyrrolidine-2-carboxylate
• CAS: 116143-05-6
• 化学式: C₂₁H₂₅NO₇S₂
• 分子量: 467.564
• InChiKey: ANVYTUWEYPVUNT-YLJYHZDGSA-N

物化性质

• 熔点：
  122-123 °C
• 沸点：
  613.1±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allo-1-(4-tolylsulfonyl)-4-<<(4-methylphenyl)sulfonyl>oxy>-D-proline ethyl ester 在 咪唑 、 4-二甲氨基吡啶 、 锂硼氢 、 18-冠醚-6 、 氢溴酸 、 potassium carbonate 、 溶剂黄146 、 苯酚 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 118.0h， 生成 [(2R,4R)-4-(6-氨基嘌呤-9-基)吡咯烷-2-基]甲醇
  参考文献：
  名称：

  Azadideoxyadenosine: Synthesis, enzymology, and anti-HIV activity

  摘要：

  Synthesis of an azanucleoside, a new analogue of dideoxyadenosine, is described. This compound is only slowly deaminated by mammalian adenosine deaminase and it is a substrate for adenosine kinase. It exhibits in vitro anti-HIV activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.085
• 作为产物：
  描述：

  4-hydroxyproline 在 乙酸酐 、 溶剂黄146 、 三乙胺 作用下， 生成 allo-1-(4-tolylsulfonyl)-4-<<(4-methylphenyl)sulfonyl>oxy>-D-proline ethyl ester
  参考文献：
  名称：

  WO2008/134035

  摘要：

  公开号：

文献信息

• Synthesis of (1<i>R</i>,4<i>R</i>)- and (1<i>S</i>,4<i>S</i>)-2,5-Diazabicyclo[2.2.1]heptanes and Their<i>N</i>-Substituted Derivatives
  作者：Ulrich Jordis、Fritz Sauter、Suhaib M. Siddiqi、Bernhard Küenburg、Kaberi Bhattacharya

  DOI：10.1055/s-1990-27056

  日期：——

  Derivatives of the (1R,4R)- and (1S,4S)-2,5-diazabicyclo- [2.2.1]heptane ring system are prepared in enantiomerically pure form from trans-4-hydroxy-L-proline (2). The target compounds are precursors of antibacterial quinolone carboxyclic acids.

  (1R,4R)-和(1S,4S)-2,5-二氮杂双环[2.2.1]庚烷环系的衍生物以对映体纯形式从反式-4-羟基-L-脯氨酸（2）中制备而成。目标化合物是抗菌喹啉羧酸的前体。
• Fluoronaphthyridines and quinolones as antibacterial agents. 2. Synthesis and structure-activity relationships of new 1-tert-butyl 7-substituted derivatives
  作者：D. Bouzard、P. Di Cesare、M. Essiz、J. P. Jacquet、J. R. Kiechel、P. Remuzon、A. Weber、T. Oki、M. Masuyoshi

  DOI：10.1021/jm00167a010

  日期：1990.5

  A number of 7-substituted-1-tert-butyl-6-fluoroquinolone-3-carboxylic acids and 7-substituted-1-tert-butyl-6-fluoro-1,8-naphthyridine-3-carboxylic acids have been prepared and tested for antibacterial activities. Among those the 7-aminopyrrolidinyl 20b and the 7-diazabicyclo naphthyridine 18b are the most potent compounds in vitro and in vivo. Physicochemical data and acute toxicity are also discussed

  已经制备了许多7-取代的1-叔丁基-6-氟喹诺酮-3-羧酸和7-取代的1-叔丁基-6-氟-1,8-萘啶-3-羧酸。经测试具有抗菌活性。其中7-氨基吡咯烷基20b和7-二氮杂双环萘啶18b是体外和体内最有效的化合物。还讨论了理化数据和急性毒性。考虑到体外和体内的微生物活性，低毒性和药代动力学特征，化合物18b BMY 40062表现出最有利的总体性能，并被选择用于临床评估。
• FUSED PYRAZINE COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE AND INFLAMMATORY DISEASES
  申请人：Andrews Martin James Inglis

  公开号：US20090286798A1

  公开（公告）日：2009-11-19

  Novel[1.2.4]triazolo[1,5-a]pyrazine and imidazo[1,2-a]pyrazine compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, and others.

  揭示了具有以下表示的公式的新型[1.2.4]三唑并咪唑[1,2-a]吡嗪化合物：这些化合物可以制备为药物组合物，并可用于哺乳动物包括人类的预防和治疗多种疾病，包括但不限于疼痛、炎症等。
• Substituted triazolopyrazines useful for the treatment of degenerative and inflammatory diseases
  申请人：Galapagos NV

  公开号：US08012983B2

  公开（公告）日：2011-09-06

  Novel [1.2.4]triazolo[1,5-a]pyrazine and imidazo[1,2-a]pyrazine compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, and others.

  本发明揭示了一种具有以下代表性公式的Novel [1.2.4]triazolo[1,5-a]pyrazine和imidazo[1,2-a]pyrazine化合物：这些化合物可以制备为药物组合物，可以用于预防和治疗哺乳动物包括人类的各种疾病，例如但不限于疼痛、炎症等。
• Synthesis of (S,S)- and (R,R)-2-alkyl-2,5-diazabicyclo[2.2.1]heptanes
  作者：Tamim F. Braish、Darrell E. Fox

  DOI：10.1021/jo00292a054

  日期：1990.3