Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-6-((3S,4R,5R)-4-acetoxy-5-benzyloxymethyl-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester | 219530-57-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-6-((3S,4R,5R)-4-acetoxy-5-benzyloxymethyl-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4S)-4-[(2S,3R,4S,5R,6R)-4,5-diacetyloxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-(phenylmethoxymethyl)oxolan-3-yl] acetate
• CAS: 219530-57-1
• 化学式: C₃₈H₄₄O₁₂
• 分子量: 692.76
• InChiKey: UQIYSRISXGRBMO-IXBUKYTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-6-((3S,4R,5R)-4-acetoxy-5-benzyloxymethyl-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester 在 四氮唑 、 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 Phosphoric acid dibenzyl ester (2R,3R,4R,5R,6S)-5-benzyloxy-2-benzyloxymethyl-6-[(3S,4R,5R)-5-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
• 作为产物：
  描述：

  乙酸酐 、 (2R,3S,4S,5R,6R)-5-Benzyloxy-2-benzyloxymethyl-6-((3S,4R,5R)-5-benzyloxymethyl-4-hydroxy-tetrahydro-furan-3-yloxy)-tetrahydro-pyran-3,4-diol 在 吡啶 作用下， 反应 15.0h， 生成 Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-6-((3S,4R,5R)-4-acetoxy-5-benzyloxymethyl-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-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