(S)-9-Benzyloxy-nonane-1,2,5-triol | 264197-66-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-9-Benzyloxy-nonane-1,2,5-triol
• 英文别名: (2S)-9-phenylmethoxynonane-1,2,5-triol
• CAS: 264197-66-2
• 化学式: C₁₆H₂₆O₄
• 分子量: 282.38
• InChiKey: ACKYBBCIBROTAE-LYKKTTPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-9-Benzyloxy-nonane-1,2,5-triol 在 sodium chlorite 、 sodium dihydrogenphosphate 、 palladium on activated charcoal 、 草酰氯 、 偶氮二甲酸二异丙酯 、 氢气 、 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 、 叔丁醇 为溶剂， 反应 65.5h， 生成 (S)-2-Benzyloxycarbonylamino-3-{[(2R,5R)-5-(4-guanidino-butyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Integrin Antagonists Containingtrans- andcis-2,5-Disubstituted THF Rings

  摘要：

  The synthesis of a series of RGD mimetics is described. All compounds consist of a central 2,5-disubstituted tetrahydrofuran core, a variable linker to a guanidino group, and a beta-amino alanine unit to mimic the carboxylic acid. Three types of linkers were investigated: a simple four-atom methylene chain (type A, compounds 14, 15, 16, and 17), a four-atom methylene chain with an additional chiral center, and a nitrogen substituent (type B, compounds 38, 39, and 40), and an amide linker of different length with an additional chiral center (type C, compounds 59, 60, 61 and 62). A variety of compounds were tested as potential integrin antagonists in a receptor binding assay (alpha(IIb)beta(3), alpha(v)beta(3), and alpha(v)beta(5)). The relative and absolute configuration of the chiral centers at the THF ring had a pronounced effect on the binding activity and selectivity Compound 14 proved to be a selective inhibitor of to be a selective inhibitor of to be a selective inhibitor of alpha(IIb)beta(3) (IC50 = 20nM), whereas compound 40 exhibited high activity for binding of alpha(IIb)beta(3) (IC50 = 67 nM) and alpha(v)beta(3) (IC50 = 52 nM).

  DOI：

  10.1002/(sici)1521-3765(20000218)6:4<666::aid-chem666>3.0.co;2-z
• 作为产物：
  描述：

  5-benzyloxy-1-pentanal 在 盐酸 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 (S)-9-Benzyloxy-nonane-1,2,5-triol
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Integrin Antagonists Containingtrans- andcis-2,5-Disubstituted THF Rings

  摘要：

  The synthesis of a series of RGD mimetics is described. All compounds consist of a central 2,5-disubstituted tetrahydrofuran core, a variable linker to a guanidino group, and a beta-amino alanine unit to mimic the carboxylic acid. Three types of linkers were investigated: a simple four-atom methylene chain (type A, compounds 14, 15, 16, and 17), a four-atom methylene chain with an additional chiral center, and a nitrogen substituent (type B, compounds 38, 39, and 40), and an amide linker of different length with an additional chiral center (type C, compounds 59, 60, 61 and 62). A variety of compounds were tested as potential integrin antagonists in a receptor binding assay (alpha(IIb)beta(3), alpha(v)beta(3), and alpha(v)beta(5)). The relative and absolute configuration of the chiral centers at the THF ring had a pronounced effect on the binding activity and selectivity Compound 14 proved to be a selective inhibitor of to be a selective inhibitor of to be a selective inhibitor of alpha(IIb)beta(3) (IC50 = 20nM), whereas compound 40 exhibited high activity for binding of alpha(IIb)beta(3) (IC50 = 67 nM) and alpha(v)beta(3) (IC50 = 52 nM).

  DOI：

  10.1002/(sici)1521-3765(20000218)6:4<666::aid-chem666>3.0.co;2-z