2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside | 912567-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-4-acetyloxy-6-[(2R,3S,4S)-2-benzyl-4-hydroxyoxolan-3-yl]oxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 912567-61-4
• 化学式: C₃₅H₄₀O₁₀
• 分子量: 620.697
• InChiKey: IVTMCICZBPDYQZ-ITNRGQBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside 在 sodium methylate 、 咪唑 三氟甲磺酸盐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Adenophostin A Analogues Conjugating an Aromatic Group at the 5‘-Position as Potent IP₃ Receptor Ligands

  摘要：

  Previous structure-activity relationship studies of adenophostin A, a potent IP3 receptor agonist, led us to design the novel adenophostin A analogues 5a-c, conjugating an aromatic group at the 5'-position to develop useful IP3 receptor ligands. The common key intermediate, a D-ribosyl alpha-D-glucoside 10 alpha, was stereoselectively synthesized by a glycosidation with the 1-sulfinylglucoside donor 11, which was conformationally restricted by a 3,4-O-cyclic diketal protecting group. After introduction of an aromatic group at the 5-position of the ribose moiety, an adenine base was stereoselectively introduced at the anomeric beta-position to form 7a-c, where the tetra-O-i-butyryl donors 9a-c were significantly more effective than the corresponding O-acetyl donor. Thus, the target compounds 5a-c were synthesized via phosphorylation of the 2', 3", and 4"-hydroxyls. The potencies of compounds 5a-c for Ca2+ release were shown to be indistinguishable from that of adenophostin A, indicating that bulky substitutions at the 5'-position of adenophostin A are well-tolerated in the receptor binding. This biological activity of 5a-c can be rationalized by molecular modeling using the ligand binding domain of the IP3 receptor.

  DOI：

  10.1021/jm060310d
• 作为产物：
  描述：

  3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-phenyl-α-D-ribofuranose 在 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 三乙胺 、 三氟乙酸 、 硫代氯甲酸苯酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.33h， 生成 2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Adenophostin A Analogues Conjugating an Aromatic Group at the 5‘-Position as Potent IP₃ Receptor Ligands

  摘要：

  Previous structure-activity relationship studies of adenophostin A, a potent IP3 receptor agonist, led us to design the novel adenophostin A analogues 5a-c, conjugating an aromatic group at the 5'-position to develop useful IP3 receptor ligands. The common key intermediate, a D-ribosyl alpha-D-glucoside 10 alpha, was stereoselectively synthesized by a glycosidation with the 1-sulfinylglucoside donor 11, which was conformationally restricted by a 3,4-O-cyclic diketal protecting group. After introduction of an aromatic group at the 5-position of the ribose moiety, an adenine base was stereoselectively introduced at the anomeric beta-position to form 7a-c, where the tetra-O-i-butyryl donors 9a-c were significantly more effective than the corresponding O-acetyl donor. Thus, the target compounds 5a-c were synthesized via phosphorylation of the 2', 3", and 4"-hydroxyls. The potencies of compounds 5a-c for Ca2+ release were shown to be indistinguishable from that of adenophostin A, indicating that bulky substitutions at the 5'-position of adenophostin A are well-tolerated in the receptor binding. This biological activity of 5a-c can be rationalized by molecular modeling using the ligand binding domain of the IP3 receptor.

  DOI：

  10.1021/jm060310d