(2S,3R)-2-amino-3-methoxy-3-phenylpropanoic acid | 874894-76-5

• 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: (2S,3R)-2-amino-3-methoxy-3-phenylpropanoic acid
• 英文别名: β-methoxyphenylalanine；(betaR)-beta-Methoxy-L-phenylalanine
• CAS: 874894-76-5
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: KKXIHXAQVMPMHW-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-amino-3-methoxy-3-phenylpropanoic acid 在 sodium hydroxide 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 6.0h， 生成 (2S,3R)-N-(tert-butyloxycarbonyl)-3-methoxyphenylalanine methyl ester
  参考文献：
  名称：

  Total Synthesis of Cyclomarin C

  摘要：

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.

  DOI：

  10.1021/ol049065n
• 作为产物：
  描述：

  phthaloyl-L-phenylalanyl chloride 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 一水合肼 、 silver(l) oxide 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 (2S,3R)-2-amino-3-methoxy-3-phenylpropanoic acid
  参考文献：
  名称：

  Total Synthesis of Cyclomarin C

  摘要：

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.

  DOI：

  10.1021/ol049065n

文献信息

• A stereoselective synthesis of (2S,3R)-β-methoxyphenylalanine: a component of cyclomarin A
  作者：Darren B. Hansen、Madeleine M. Joullié

  DOI：10.1016/j.tetasy.2005.10.029

  日期：2005.12

  A stereoselective synthesis of (2S,3R)-beta-methoxyphenylalanine, an amino acid contained within the cyclic peptide cyclomarin A, was successfully synthesized from Lajoie's serine aldehyde. (c) 2005 Elsevier Ltd. All rights reserved.
• Total Synthesis of Cyclomarin C
  作者：Shi-Jun Wen、Zhu-Jun Yao

  DOI：10.1021/ol049065n

  日期：2004.8.1

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.