(-)-(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(1Z)-prop-1-enyl]pyrrolidine-2-carboxylic acid | 335679-69-1

• 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: (-)-(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(1Z)-prop-1-enyl]pyrrolidine-2-carboxylic acid
• 英文别名: (5R)-((1R)-acetylamino-(2S)-methoxy-(2S)-methylpentyl)-(4S)-Z-propenylpyrrolidine-(2R)-carboxylic acid；5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(1Z)-1-propenyl]-(4S,5R)-D-proline；A-315675；(+/-)-(2R,3S,5R,1'R,2'S)-2-(1-Acetamido-2-methyl-2-methoxy)pentyl-3-(cis-propen-1-yl)-pyrrolidine-5-carboxylic Acid；D-Proline, 5-((1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl)-4-(1Z)-1-propenyl-, (4S,5R)-；(2R,4S,5R)-5-[(1R,2S)-1-acetamido-2-methoxy-2-methylpentyl]-4-[(Z)-prop-1-enyl]pyrrolidine-2-carboxylic acid
• CAS: 335679-69-1
• 化学式: C₁₇H₃₀N₂O₄
• 分子量: 326.436
• InChiKey: UUVKABIGWGMYCE-FLMGFEAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-戊醇 、 (-)-(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(1Z)-prop-1-enyl]pyrrolidine-2-carboxylic acid 在 ammonium hydroxide 、 氯化亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2R,3S,5R,1'R,2'S)-2-(1-Acetamido-2-methoxy-2-methyl)pentyl-3-(cis-propen-1-yl)pyrrolidine-5-carboxylic Acid 3-Pentyl Ester
  参考文献：
  名称：

  Inhibitors of neuraminidases

  摘要：

  揭示了以下式的化合物，这些化合物对抑制疾病致病微生物的神经氨酸酶，特别是流感神经氨酸酶，具有用处。还揭示了预防和治疗由具有神经氨酸酶的微生物引起的疾病的组合物和方法，以及用于制备这些化合物和合成中间体的过程。

  公开号：

  US06455571B1
• 作为产物：
  描述：

  (2E)-2-methyl-2-penten-1-ol 在 4 A molecular sieve titanium(IV) isopropylate 、 盐酸 、 甲醇 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 D-(-)-酒石酸二甲酯 、 4 A molecular sieve 、 Celite 、 三氟化硼乙醚 、 氢气 、 sodium hexamethyldisilazane 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二异丁基氢化铝 、 magnesium sulfate 、 magnesium 、 1,2-二溴乙烷 、 三乙胺 、 pyridinium chlorochromate 、 三甲氧基磷 作用下， 以 四氢呋喃 、 乙醚 、 癸烷 、 正己烷 、 二氯甲烷 为溶剂， 反应 132.42h， 生成 (-)-(2R,4S,5R)-5-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-4-[(1Z)-prop-1-enyl]pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Enantioselective Synthesis of Antiinfluenza Compound A-315675

  摘要：

  Drug discovery efforts at Abbott Laboratories have led to the identification of influenza neuraminidase inhibitor A-315675 (1) as a candidate for development as an antiinfluenza drug. A convergent, stereoselective synthesis of this highly functionalized pyrrolidine is reported that utilizes pyrrolinone 2 as the key intermediate. The C5, C6 stereochemistry was established through a diastereoselective condensation of chiral imine compound 3 with silyloxypyrrole 4 to give pyrrolinone 2. The stereochemical outcome of this reaction depended critically on the choice of the imine functional group (FG), with tritylsulfenyl and (R)-toluenesulfinyl providing the desired products in good yields as crystalline intermediates. Conversion of pyrrolinone 2 into 1 was accomplished in seven subsequent steps, including Michael addition of cis-1-propenylcuprate at C4 and introduction of a cyano group as a carboxylic acid equivalent at C2.

  DOI：

  10.1021/jo0162890

文献信息

• Total Synthesis of A-315675:  A Potent Inhibitor of Influenza Neuraminidase
  作者：Stephen Hanessian、Malken Bayrakdarian、Xuehong Luo

  DOI：10.1021/ja0126226

  日期：2002.5.1

  A concise, stereocontrolled, and practical synthesis of a neuraminidase inhibitor consisting of a highly functionalized D-proline scaffold is described. Key features involve a stereocontrolled addition of a propiolate ester to a chiral nonracemic nitrone derived originally from D-serine and the manipulation of acyclic and cyclic motifs en route to the target in 12.8% overall yield over 22 steps. Several

  描述了由高度功能化的 D-脯氨酸支架组成的神经氨酸酶抑制剂的简洁、立体控制和实用的合成。主要特征包括将丙炔酸酯立体控制添加到最初衍生自 D-丝氨酸的手性非外消旋硝酮中，以及在通往目标的途中以 12.8% 的总产率在 22 个步骤中操纵无环和环状基序。几种结晶中间体适用于单晶 X 射线分析。
• Total synthesis of A-315675 based on the cascade Overman rearrangement
  作者：Takayuki Momose、Naoto Hama、Chiharu Higashino、Hideyuki Sato、Noritaka Chida

  DOI：10.1016/j.tetlet.2007.12.080

  日期：2008.2

  The chiral and stereoselective total synthesis of A-315675 1, an antiinfluenza agent, is described. The vicinal diamino moiety in 1 was stereoselectively constructed by the cascade Overman rearrangement of a vicinal allylic-homoallylic diol derived from D-tartrate. (c) 2007 Elsevier Ltd. All rights reserved.
• BIOPROCESSING
  申请人：Rossomando Anthony

  公开号：US20140154783A1

  公开（公告）日：2014-06-05

  The present invention relates to molecular biology, molecular genetics, and bioprocessing. The embodiments provide for compositions and methods for producing a biological product, such as an immunogenic agent, in an embryonated egg by introducing into the egg a RNA effector molecule capable of modulating expression of a target gene, wherein the modulation enhances production of the biological product in the egg. These methods provide for RNAi-based approaches to optimize the production of biologics from embryonated eggs, such as the production of viral vaccines including seasonal and pandemic flu vaccines. The invention also relates to molecules, reagents, cells, and kits useful for carrying out the methods, and biological products produced by the methods.
• METHODS AND COMPOSITIONS COMPRISING AKT INHIBITORS AND/OR PHOSPHOLIPASE D INHIBITORS
  申请人：Vanderbilt University

  公开号：US20140378524A1

  公开（公告）日：2014-12-25

  Disclosed are methods of treating viral infections or disorders of uncontrolled proliferation comprising, in one aspect, administering compounds that are phospholipase D inhibitors and/or Akt therapeutic agents. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
• ANTIVIRAL THERAPIES WITH PHOSPHOLIPASE D INHIBITORS
  申请人：Lindsley Craig W.

  公开号：US20150025041A1

  公开（公告）日：2015-01-22

  Disclosed are methods of treating viral infections comprising, in one aspect, administering compounds that are phospholipase D inhibitors. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention. In accordance with the purpose(s) of the invention, as embodied and broadly described herein, the invention, in one aspect, relates to antiviral therapies. For example, compounds having Phospholipase D activity (e.g., isoform selective Phospholipase D inhibitors) can be useful in antiviral therapies (e.g., influenza treatments).