6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-4-(diethoxy-phosphoryloxy)-tetrahydro-pyran-2S-carboxylic acid methyl ester | 623143-67-9

• 分子结构分类: 有机化合物
• 英文名称: 6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-4-(diethoxy-phosphoryloxy)-tetrahydro-pyran-2S-carboxylic acid methyl ester
• CAS: 623143-67-9
• 化学式: C₂₅H₃₇N₂O₉P
• 分子量: 540.551
• InChiKey: JXAHXWHHVPETAO-MMCLJHOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  142.41
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-4-(diethoxy-phosphoryloxy)-tetrahydro-pyran-2S-carboxylic acid methyl ester 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以69%的产率得到6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-tetrahydro-pyran-2S-carboxylic acid methyl ester
  参考文献：
  名称：

  Novel tetrahydropyran-based peptidomimetics from a bioisosteric transformation of a tripeptide. Evidence of their activity at melanocortin receptors

  摘要：

  We have prepared novel peptidomimetics based on a 2,4,6-trisubstituted tetrahydropyran. This scaffold was constructed in an isosteric transformation using conceptual constraints imposed on a tripeptide moiety involving O-i'-C-1(+1)gamma and O-i'-Ni+2 formal cyclization modes. A series of regioselective transformations commencing with a substituted dihydropyran-4-one readily provided the required analogues. Specific tetrahydropyrane analogues modeled on PheArgTrp as a truncated version of the melanocortin receptor message sequence, showed activity at the melanocortin receptors MC4R and MC1R. Thus, the 2,4,6-trisubstituted tetrahydropyran scaffold has provided a potentially useful peptidomimetic lead, and conceptual cyclization of peptide moieties can offer a valuable design strategy in peptidomimetic research. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00274-8
• 作为产物：
  描述：

  [1-(6R-cyano-4-oxo-tetrahydro-pyran-2R-yl)-2R-phenylethyl]carbamic acid tert-butyl ester 在 氢氧化钾 、 氰化钠 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-4-(diethoxy-phosphoryloxy)-tetrahydro-pyran-2S-carboxylic acid methyl ester
  参考文献：
  名称：

  Novel tetrahydropyran-based peptidomimetics from a bioisosteric transformation of a tripeptide. Evidence of their activity at melanocortin receptors

  摘要：

  We have prepared novel peptidomimetics based on a 2,4,6-trisubstituted tetrahydropyran. This scaffold was constructed in an isosteric transformation using conceptual constraints imposed on a tripeptide moiety involving O-i'-C-1(+1)gamma and O-i'-Ni+2 formal cyclization modes. A series of regioselective transformations commencing with a substituted dihydropyran-4-one readily provided the required analogues. Specific tetrahydropyrane analogues modeled on PheArgTrp as a truncated version of the melanocortin receptor message sequence, showed activity at the melanocortin receptors MC4R and MC1R. Thus, the 2,4,6-trisubstituted tetrahydropyran scaffold has provided a potentially useful peptidomimetic lead, and conceptual cyclization of peptide moieties can offer a valuable design strategy in peptidomimetic research. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00274-8