(2R,5S,αR)-5-[4'-benzyloxy-α-methoxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine | 864954-50-7

• 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: (2R,5S,αR)-5-[4'-benzyloxy-α-methoxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine
• 英文别名: (2S,5R)-3,6-dimethoxy-2-[(R)-methoxy-(4-phenylmethoxyphenyl)methyl]-5-propan-2-yl-2,5-dihydropyrazine
• CAS: 864954-50-7
• 化学式: C₂₄H₃₀N₂O₄
• 分子量: 410.513
• InChiKey: BIQQKNVUTBPKTJ-BHIFYINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,5S,αR)-5-[4'-benzyloxy-α-methoxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine 在 盐酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 16.0h， 以71%的产率得到(R)-O-benzyl-β-methoxy-L-tyrosine methyl ester
  参考文献：
  名称：

  Complete Stereochemistry of Neamphamide A and Absolute Configuration of the β-Methoxytyrosine Residue in Papuamide B

  摘要：

  [GRAPHICS]The absolute stereochemistry of the three unresolved structural components in neamphamide A (1) was determined to be (R)-beta-methoxy-L-tyrosine, (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid, and (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid. Stereochemical assignments were made by chemical degradation of 1, derivatization of the resulting products, and then spectroscopic and chromatographic comparison of the derivatives with synthetically prepared standards. Using the same analytical protocol developed for 1, the beta-methoxytyrosine residue in papuamide B (2) was found to be (R)-beta-methoxy-D-tyrosine. This represents a rare example of divergent stereochemistry in an unusual amino acid residue that is present in two closely related classes of peptides.

  DOI：

  10.1021/jo0508853
• 作为产物：
  描述：

  4-苄氧基苯甲醛 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 (2R,5S,αR)-5-[4'-benzyloxy-α-methoxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine
  参考文献：
  名称：

  Complete Stereochemistry of Neamphamide A and Absolute Configuration of the β-Methoxytyrosine Residue in Papuamide B

  摘要：

  [GRAPHICS]The absolute stereochemistry of the three unresolved structural components in neamphamide A (1) was determined to be (R)-beta-methoxy-L-tyrosine, (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid, and (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid. Stereochemical assignments were made by chemical degradation of 1, derivatization of the resulting products, and then spectroscopic and chromatographic comparison of the derivatives with synthetically prepared standards. Using the same analytical protocol developed for 1, the beta-methoxytyrosine residue in papuamide B (2) was found to be (R)-beta-methoxy-D-tyrosine. This represents a rare example of divergent stereochemistry in an unusual amino acid residue that is present in two closely related classes of peptides.

  DOI：

  10.1021/jo0508853

文献信息

• Complete Stereochemistry of Neamphamide A and Absolute Configuration of the β-Methoxytyrosine Residue in Papuamide B
  作者：Naoya Oku、Ravi Krishnamoorthy、Alan G. Benson、Robert L. Ferguson、Mark A. Lipton、Lawrence R. Phillips、Kirk R. Gustafson、James B. McMahon

  DOI：10.1021/jo0508853

  日期：2005.8.1

  [GRAPHICS]The absolute stereochemistry of the three unresolved structural components in neamphamide A (1) was determined to be (R)-beta-methoxy-L-tyrosine, (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid, and (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid. Stereochemical assignments were made by chemical degradation of 1, derivatization of the resulting products, and then spectroscopic and chromatographic comparison of the derivatives with synthetically prepared standards. Using the same analytical protocol developed for 1, the beta-methoxytyrosine residue in papuamide B (2) was found to be (R)-beta-methoxy-D-tyrosine. This represents a rare example of divergent stereochemistry in an unusual amino acid residue that is present in two closely related classes of peptides.