(2R,3R,4S,5R,6R)-2-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-6-(1-benzenesulfonyl-1H-pyrrol-2-ylmethoxymethyl)-4-benzyloxy-tetrahydro-pyran-3,5-diol | 850249-39-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-2-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-6-(1-benzenesulfonyl-1H-pyrrol-2-ylmethoxymethyl)-4-benzyloxy-tetrahydro-pyran-3,5-diol
• CAS: 850249-39-7
• 化学式: C₄₀H₄₀N₂O₁₀S₂
• 分子量: 772.897
• InChiKey: LBMVMCSOQNCSSZ-PFWGIBHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  54.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  155.52
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-6-(1-benzenesulfonyl-1H-pyrrol-2-ylmethoxymethyl)-4-benzyloxy-tetrahydro-pyran-3,5-diol 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以70%的产率得到(2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-[2-(1H-indol-3-yl)-ethoxy]-tetrahydro-pyran-3,5-diol
  参考文献：
  名称：

  Synthesis and Binding Affinities of Novel SRIF-Mimicking β-d-Glucosides Satisfying the Requirement for a π-Cloud at C1

  摘要：

  The synthesis of four bioactive analogues of the somatostatin (SRIF-14) mimetic, beta-D-glucoside (+)-2, in which the C1 indole side chain is replaced with indole surrogates, has been achieved. These congeners, possessing the naphthyl, benzothiophene, benzyl, and benzofuran substituents, were predicted to satisfy the electrostatic requirements of the tryptophan binding pocket of SRIF. Unlike the previously described C4 picolyl and pyrazinyl congeners, these ligands bind the hSST4 receptor.

  DOI：

  10.1021/ol050119i
• 作为产物：
  描述：

  (4aR,6R,7R,8R,8aR)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-2-(1-benzenesulfonyl-1H-pyrrol-2-yl)-8-benzyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 以55%的产率得到(2R,3R,4S,5R,6R)-2-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-6-(1-benzenesulfonyl-1H-pyrrol-2-ylmethoxymethyl)-4-benzyloxy-tetrahydro-pyran-3,5-diol
  参考文献：
  名称：

  Synthesis and Binding Affinities of Novel SRIF-Mimicking β-d-Glucosides Satisfying the Requirement for a π-Cloud at C1

  摘要：

  The synthesis of four bioactive analogues of the somatostatin (SRIF-14) mimetic, beta-D-glucoside (+)-2, in which the C1 indole side chain is replaced with indole surrogates, has been achieved. These congeners, possessing the naphthyl, benzothiophene, benzyl, and benzofuran substituents, were predicted to satisfy the electrostatic requirements of the tryptophan binding pocket of SRIF. Unlike the previously described C4 picolyl and pyrazinyl congeners, these ligands bind the hSST4 receptor.

  DOI：

  10.1021/ol050119i