Phosphoric acid dibenzyl ester (2R,3R,4R,5R,6R)-5-benzyloxy-2-benzyloxymethyl-6-[(2R,3R,4S)-2-benzyloxymethyl-4-(bis-benzyloxy-phosphoryloxy)-tetrahydro-furan-3-yloxy]-4-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-3-yl ester | 219530-47-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phosphoric acid dibenzyl ester (2R,3R,4R,5R,6R)-5-benzyloxy-2-benzyloxymethyl-6-[(2R,3R,4S)-2-benzyloxymethyl-4-(bis-benzyloxy-phosphoryloxy)-tetrahydro-furan-3-yloxy]-4-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-3-yl ester
• 英文别名: dibenzyl [(3S,4R,5R)-4-[(2R,3R,4R,5R,6R)-4,5-bis[bis(phenylmethoxy)phosphoryloxy]-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-5-(phenylmethoxymethyl)oxolan-3-yl] phosphate
• CAS: 219530-47-9
• 化学式: C₇₄H₇₇O₁₈P₃
• 分子量: 1347.34
• InChiKey: KLVXEXJWLQKJJB-UEAXAMRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  95
• 可旋转键数：
  37
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  190
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  Phosphoric acid dibenzyl ester (2R,3R,4R,5R,6R)-5-benzyloxy-2-benzyloxymethyl-6-[(2R,3R,4S)-2-benzyloxymethyl-4-(bis-benzyloxy-phosphoryloxy)-tetrahydro-furan-3-yloxy]-4-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-3-yl ester 在 palladium on activated charcoal WK-20 resin column (Na⁺ form) 、 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以100%的产率得到(2R,3R,4S)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl α-D-glucopyranoside 3,4,4'-trisphosphate hexasodium salt
  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：

  (2R,3R,4S,5R)-3,4-Bis-allyloxy-6-((2R,3S,4S)-4-allyloxy-2-benzyloxymethyl-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran 在 palladium on activated charcoal 吡啶 、 四氮唑 、 sodium methylate 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 32.0h， 生成 Phosphoric acid dibenzyl ester (2R,3R,4R,5R,6R)-5-benzyloxy-2-benzyloxymethyl-6-[(2R,3R,4S)-2-benzyloxymethyl-4-(bis-benzyloxy-phosphoryloxy)-tetrahydro-furan-3-yloxy]-4-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-3-yl ester
  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