1,4-anhydro-2-O-benzoyl-5-O-benzyl-3-O-(4-methoxybenzyl)-D-ribitol | 219530-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-anhydro-2-O-benzoyl-5-O-benzyl-3-O-(4-methoxybenzyl)-D-ribitol
• 英文别名: [(3S,4R,5R)-4-[(4-methoxyphenyl)methoxy]-5-(phenylmethoxymethyl)oxolan-3-yl] benzoate
• CAS: 219530-29-7
• 化学式: C₂₇H₂₈O₆
• 分子量: 448.516
• InChiKey: GVBCLPRAJPBWSH-UODIDJSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2-O-benzoyl-5-O-benzyl-3-O-(4-methoxybenzyl)-D-ribitol 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 1,4-anhydro-2,5-di-O-benzyl-3-O-(4-methoxybenzyl)-D-ribitol
  参考文献：
  名称：

  Synthesis of Adenophostin Analogues Lacking the Adenine Moiety as Novel Potent IP₃ Receptor Ligands:  Some Structural Requirements for the Significant Activity of Adenophostin A

  摘要：

  1-O-Tetrahydrofuranyl-alpha-D-glucopyranose derivatives 5-8 were designed and synthesized as novel IP3 receptor ligands. The glycosidation reactions between fluoroglycosyl donor 23 and tetrahydrofuran derivatives 11-14 as glycosyl accepters selectively gave the corresponding alpha-glycosides, which were converted into the target Compounds 5-8 via the introduction of phosphate groups using the phosphoramidite method. Among these compounds, 1-O-tetrahydrofuranyl-alpha-D-glucopyranose trisphosphate derivatives 5 and 8 significantly inhibited the binding of [H-3] IP3 to IP3 receptor from porcine cerebella, with IC50 values of 25 and 27 nM, respectively, which were comparable to the affinity of IP3 itself.

  DOI：

  10.1021/jo980925l
• 作为产物：
  描述：

  苯甲酰氯 、 1,4-anhydro-5-O-benzyl-3-O-(4-methoxybenzyl)-D-ribitol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,4-anhydro-2-O-benzoyl-5-O-benzyl-3-O-(4-methoxybenzyl)-D-ribitol
  参考文献：
  名称：

  Synthesis of Adenophostin Analogues Lacking the Adenine Moiety as Novel Potent IP₃ Receptor Ligands:  Some Structural Requirements for the Significant Activity of Adenophostin A

  摘要：

  1-O-Tetrahydrofuranyl-alpha-D-glucopyranose derivatives 5-8 were designed and synthesized as novel IP3 receptor ligands. The glycosidation reactions between fluoroglycosyl donor 23 and tetrahydrofuran derivatives 11-14 as glycosyl accepters selectively gave the corresponding alpha-glycosides, which were converted into the target Compounds 5-8 via the introduction of phosphate groups using the phosphoramidite method. Among these compounds, 1-O-tetrahydrofuranyl-alpha-D-glucopyranose trisphosphate derivatives 5 and 8 significantly inhibited the binding of [H-3] IP3 to IP3 receptor from porcine cerebella, with IC50 values of 25 and 27 nM, respectively, which were comparable to the affinity of IP3 itself.

  DOI：

  10.1021/jo980925l