2-benzyl-4-tetrahydrofuran-3-yl 2,6-di-O-benzyl-α-D-glucopyranoside | 912567-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzyl-4-tetrahydrofuran-3-yl 2,6-di-O-benzyl-α-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-6-[(2R,3S,4S)-2-benzyl-4-hydroxyoxolan-3-yl]oxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxane-3,4-diol
• CAS: 912567-62-5
• 化学式: C₃₁H₃₆O₈
• 分子量: 536.622
• InChiKey: SGJVXGHJQMHTAN-VAZHLXPHSA-N

物化性质

• 沸点：
  721.6±60.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-benzyl-4-tetrahydrofuran-3-yl 2,6-di-O-benzyl-α-D-glucopyranoside 在 钯 氢气 、 咪唑 三氟甲磺酸盐 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， -40.0~20.0 ℃ 、413.68 kPa 条件下， 生成 (2R,3R,4S)-2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-α-D-glucopyranoside trisphosphate
  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：

  1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside 在 三乙基硅烷 、 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 sodium methylate 、 三乙胺 、 三氟乙酸 、 硫代氯甲酸苯酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 8.33h， 生成 2-benzyl-4-tetrahydrofuran-3-yl 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

文献信息

• Synthesis of Adenophostin A Analogues Conjugating an Aromatic Group at the 5‘-Position as Potent IP₃ Receptor Ligands
  作者：Tetsuya Mochizuki、Yoshihiko Kondo、Hiroshi Abe、Stephen C. Tovey、Skarlatos G. Dedos、Colin W. Taylor、Michael Paul、Barry V. L. Potter、Akira Matsuda、Satoshi Shuto

  DOI：10.1021/jm060310d

  日期：2006.9.1

  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.