(4R)-4-benzyl-3-[(2R,3R)-3-hydroxy-2-(4-methoxyphenyl)-4-phenylmethoxybutanoyl]-1,3-oxazolidin-2-one | 570375-92-7

• 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: (4R)-4-benzyl-3-[(2R,3R)-3-hydroxy-2-(4-methoxyphenyl)-4-phenylmethoxybutanoyl]-1,3-oxazolidin-2-one
• CAS: 570375-92-7
• 化学式: C₂₈H₂₉NO₆
• 分子量: 475.541
• InChiKey: ZZYRVKCZUDYWSX-DMTNHVFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-4-benzyl-3-[(2R,3R)-3-hydroxy-2-(4-methoxyphenyl)-4-phenylmethoxybutanoyl]-1,3-oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以99%的产率得到(2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic acid
  参考文献：
  名称：

  A new synthesis of cytoxazone and its diastereomers provides key initial SAR information

  摘要：

  A short, enantioselective, and diastereoselective synthesis of cytoxazone, a Th2-selective immunomodulator from Streptomyces, is described. The route was readily adapted to the synthesis of the three other stereoisomers of natural cytoxazone. Evaluation of these compounds revealed that the stereochemical configuration of the oxazolidinone ring did not influence their biological activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00131-8
• 作为产物：
  描述：

  苄氧基乙醛 、 (R)-4-苄基-3-(2-(4-甲氧基苯基)乙酰基)恶唑烷-2-酮 在 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 作用下， 反应 1.83h， 以51%的产率得到(4R)-4-benzyl-3-[(2R,3R)-3-hydroxy-2-(4-methoxyphenyl)-4-phenylmethoxybutanoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  A new synthesis of cytoxazone and its diastereomers provides key initial SAR information

  摘要：

  A short, enantioselective, and diastereoselective synthesis of cytoxazone, a Th2-selective immunomodulator from Streptomyces, is described. The route was readily adapted to the synthesis of the three other stereoisomers of natural cytoxazone. Evaluation of these compounds revealed that the stereochemical configuration of the oxazolidinone ring did not influence their biological activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00131-8

文献信息

• A new synthesis of cytoxazone and its diastereomers provides key initial SAR information
  作者：Percy H. Carter、Jacob R. LaPorte、Peggy A. Scherle、Carl P. Decicco

  DOI：10.1016/s0960-894x(03)00131-8

  日期：2003.4

  A short, enantioselective, and diastereoselective synthesis of cytoxazone, a Th2-selective immunomodulator from Streptomyces, is described. The route was readily adapted to the synthesis of the three other stereoisomers of natural cytoxazone. Evaluation of these compounds revealed that the stereochemical configuration of the oxazolidinone ring did not influence their biological activity. (C) 2003 Elsevier Science Ltd. All rights reserved.