(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-6-(2-benzo[b]thiophen-3-yl-ethoxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran | 850249-60-4

• 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-(5-Azido-pentyloxymethyl)-6-(2-benzo[b]thiophen-3-yl-ethoxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran
• CAS: 850249-60-4
• 化学式: C₄₂H₄₇N₃O₆S
• 分子量: 721.918
• InChiKey: VILHPDLZMWGXPP-FLMPIELBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.44
• 重原子数：
  52.0
• 可旋转键数：
  21.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  104.14
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-6-(2-benzo[b]thiophen-3-yl-ethoxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以90%的产率得到5-[[(2R,3R,4S,5R,6R)-6-[2-(1-benzothiophen-3-yl)ethoxy]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]pentan-1-amine
  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：

  5-azidopentyl trifluoromethanesulfonate 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 67.0h， 生成 (2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-6-(2-benzo[b]thiophen-3-yl-ethoxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran
  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