(4R)-3-[(2R)-4-(tert-butoxy)-2-(1-methylethyl)-4-oxobutanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4R)-3-[(2R)-4-(tert-butoxy)-2-(1-methylethyl)-4-oxobutanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one
• 英文别名: (R)-tert-butyl 3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-methylpentanoate；tert-butyl (R)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-methylpentanoate；tert-butyl (3R)-3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]-4-methylpentanoate
• 化学式: C₂₁H₂₉NO₅
• 分子量: 375.465
• InChiKey: SRNCJCMKPHDEDG-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R)-3-[(2R)-4-(tert-butoxy)-2-(1-methylethyl)-4-oxobutanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one 在 lithium hydroxide monohydrate 、 dimethyl sulfide borane 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.17h， 生成 (R)-tert-butyl 3-hydroxymethyl-4-methylpentanoate
  参考文献：
  名称：

  [EN] SUBSTITUTED 2-PYRIDONE TRICYCLIC COMPOUNDS, ANALOGUES THEREOF, AND METHODS USING SAME
  [FR] COMPOSÉS TRICYCLIQUES 2-PYRIDONE SUBSTITUÉS, ANALOGUES DE CEUX-CI, ET PROCÉDÉS LES UTILISANT

  摘要：

  本发明在某一方面包括替代的2-氧代-1,2,5,6-四氢苯并[h]喹啉-3-羧酸，其类似物，以及包含其的组合物，可用于治疗和/或预防患者体内的乙型肝炎病毒（HBV）感染和/或丙型肝炎病毒（HDV）。在某些实施例中，本发明提供一种化合物，或其盐、溶剂合物、几何异构体、立体异构体、互变异构体和任何混合物。

  公开号：

  WO2019177937A1
• 作为产物：
  描述：

  异戊酸 在 正丁基锂 、 sodium hexamethyldisilazane 、 三甲基乙酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (4R)-3-[(2R)-4-(tert-butoxy)-2-(1-methylethyl)-4-oxobutanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  The synthesis of novel matrix metalloproteinase inhibitors employing the Ireland-Claisen rearrangement

  摘要：

  Matrix metalloproteinase inhibitors of general formula (1) were synthesised by a route involving an Ireland-Claisen rearrangement which enables systematic modification of the substituent alpha to the hydroxamic acid. An analogue (12c) possessing an alpha-cyclopentyl group is a potent broad spectrum inhibitor that displays high and sustained blood levels following oral dosing in both the rat and marmoset ex-vivo bioassays. This compound and analogues are also potent inhibitors of TNF alpha release. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00218-2

文献信息

• Stereoselective synthesis of Certonardolsterol D3
  作者：Biao Jiang、He-ping Shi、Min Xu、Wan-jun Wang、Wei-shan Zhou

  DOI：10.1016/j.tet.2008.07.091

  日期：2008.10

  The first stereoselective synthesis of Certonardolsterol D3 was described. Ene reaction and improved allylic oxidation were employed as key steps for efficient construction of the desired 3β,6α,15β-triol steroidal framework. The chiral side chain in Certonardolsterol D3 was finally introduced by Julia olefination.

  描述了Certonardolsterol D 3的第一个立体选择性合成。烯反应和改进的烯丙基氧化被用作有效构建所需的3β，6α，15β-三醇甾体骨架的关键步骤。最后，通过朱莉娅烯化反应引入了Certonardolsterol D 3中的手性侧链。
• Total synthesis and absolute stereochemistry of the proteasome inhibitors cystargolides A and B
  作者：Rodolfo Tello-Aburto、Liam P. Hallada、Doleshwar Niroula、Snezna Rogelj

  DOI：10.1039/c5ob01821h

  日期：——

  The absolute stereochemistry of the cystargolides was determined by total synthesis. Evaluation of synthetic cystargolides and derivatives showed that the natural (2S,3R) stereochemistry is essential for activity. Moreover, benzyl esters (−)-10 and (−)-15 were found to be about 100 times more potent, and to selectively kill MCF-7 cancerous cells.

  胱氨酸的绝对立体化学是通过全合成确定的。对合成的胱氨酸及其衍生物的评价表明，天然的（2 S，3 R）立体化学对于活性至关重要。此外，发现苄基酯（-）- 10和（-）- 15的效价高约100倍，并且可以选择性杀死MCF-7癌细胞。
• EP4180035A1
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] SUBSTITUTED 2-PYRIDONE TRICYCLIC COMPOUNDS, ANALOGUES THEREOF, AND METHODS USING SAME<br/>[FR] COMPOSÉS TRICYCLIQUES 2-PYRIDONE SUBSTITUÉS, ANALOGUES DE CEUX-CI, ET PROCÉDÉS LES UTILISANT
  申请人：ARBUTUS BIOPHARMA INC

  公开号：WO2019177937A1

  公开（公告）日：2019-09-19

  The present invention includes in one aspect substituted 2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carboxylic acids, analogues thereof, and compositions comprising the same, which can be used to treat and/or prevent hepatitis B virus (HBV) infection and/or hepatitis D virus (HDV) in a patient. In certain embodiments, the invention provides a compound, or a salt, solvate, geometric isomer, stereoisomer, tautomer, and any mixtures thereof.

  本发明在某一方面包括替代的2-氧代-1,2,5,6-四氢苯并[h]喹啉-3-羧酸，其类似物，以及包含其的组合物，可用于治疗和/或预防患者体内的乙型肝炎病毒（HBV）感染和/或丙型肝炎病毒（HDV）。在某些实施例中，本发明提供一种化合物，或其盐、溶剂合物、几何异构体、立体异构体、互变异构体和任何混合物。
• The synthesis of novel matrix metalloproteinase inhibitors employing the Ireland-Claisen rearrangement
  作者：Lisa M Pratt、R.Paul Beckett、Claire L Bellamy、Dominic J Corkill、Judy Cossins、Paul F Courtney、Stephen J Davies、Alan H Davidson、Alan H Drummond、Karen Helfrich、Christopher N Lewis、Matthew Mangan、Fionna M Martin、Karen Miller、Prakash Nayee、Michelle L Ricketts、Wayne Thomas、Richard S Todd、Mark Whittaker

  DOI：10.1016/s0960-894x(98)00218-2

  日期：1998.6

  Matrix metalloproteinase inhibitors of general formula (1) were synthesised by a route involving an Ireland-Claisen rearrangement which enables systematic modification of the substituent alpha to the hydroxamic acid. An analogue (12c) possessing an alpha-cyclopentyl group is a potent broad spectrum inhibitor that displays high and sustained blood levels following oral dosing in both the rat and marmoset ex-vivo bioassays. This compound and analogues are also potent inhibitors of TNF alpha release. (C) 1998 Elsevier Science Ltd. All rights reserved.