{1R-[6S-(3-hydroxy-propyl)-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester | 623143-77-1

• 分子结构分类: 有机化合物
• 英文名称: {1R-[6S-(3-hydroxy-propyl)-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
• CAS: 623143-77-1
• 化学式: C₃₂H₄₁NO₅
• 分子量: 519.681
• InChiKey: AQDOHNUIUYPPOX-JHNIELBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  {1R-[6S-(3-hydroxy-propyl)-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 在 偶氮二甲酸二异丙酯 、 水 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-{3-[(2S,6R)-6-((R)-1-Amino-2-phenyl-ethyl)-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propyl}-guanidine
  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：

  (1R-{6S-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-oxo-tetrahydro-pyran-2R-yl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester 在 L-Selectride 、 sodium hydride 、 溶剂黄146 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 {1R-[6S-(3-hydroxy-propyl)-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl 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