(2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic acid | 461644-54-2

• 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: (2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic acid
• 英文别名: (2R,3R)-3-hydroxy-2-(4-methoxyphenyl)-4-phenylmethoxybutanoic acid
• CAS: 461644-54-2
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: VWUAMMQXJDHDEN-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-4-benzyloxy-3-hydroxy-2-(4-methoxyphenyl)butanoic acid 在 叠氮磷酸二苯酯 作用下， 以 二氯甲烷 为溶剂， 反应 12.67h， 以61%的产率得到(4S,5R)-4-(4-methoxyphenyl)-5-(phenylmethoxymethyl)-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
• 作为产物：
  描述：

  (R)-4-苄基-3-(2-(4-甲氧基苯基)乙酰基)恶唑烷-2-酮 在 lithium hydroxide 、 三氟甲磺酸二丁硼 、 双氧水 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 生成 (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

文献信息

• Stereoselective synthesis of (−)-cytoxazone
  作者：Miguel Carda、Florenci González、Richard Sánchez、J.Alberto Marco

  DOI：10.1016/s0957-4166(02)00227-6

  日期：2002.6

  The stereoselective synthesis of the cytokine modulator (−)-cytoxazone in enantiopure form is described. Key steps of the process are a syn-stereoselective aldol addition of a chiral ketone mediated by chlorodicyclohexylborane, and a Curtius rearrangement.

  描述了对映体纯形式的细胞因子调节剂（-）-cytoxazone的立体选择性合成。该方法的关键步骤是由氯二环己基硼烷介导的手性酮的顺式-立体选择性羟醛加成和Curtius重排。
• 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.