2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-phenylsulfinyl-β-D-glucopyranoside | 518332-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-phenylsulfinyl-β-D-glucopyranoside
• CAS: 518332-41-7
• 化学式: C₃₂H₃₈O₈S
• 分子量: 582.715
• InChiKey: XOVKLTFXHPMLRX-WASHZWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-phenylsulfinyl-β-D-glucopyranoside 在 吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 4 A molecular sieve 、 四丁基氟化铵 、 二甲基亚砜 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 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
  参考文献：
  名称：

  Design and Synthesis of 5‘-Deoxy-5‘-Phenyladenophostin A, a Highly Potent IP₃ Receptor Ligand¹

  摘要：

  5'-Deoxy-5'-phenyladenophostin A (5), designed as a useful IP3 receptor ligand based on the previous structure-activity relationship studies, was successfully synthesized via two key stereoselective glycosidation steps. This compound proved to be a highly potent IP3 receptor agonist.

  DOI：

  10.1021/ol0602710
• 作为产物：
  描述：

  phenyl 3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-thio-β-D-glucopyranoside 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-phenylsulfinyl-β-D-glucopyranoside
  参考文献：
  名称：

  Design and Synthesis of 5‘-Deoxy-5‘-Phenyladenophostin A, a Highly Potent IP₃ Receptor Ligand¹

  摘要：

  5'-Deoxy-5'-phenyladenophostin A (5), designed as a useful IP3 receptor ligand based on the previous structure-activity relationship studies, was successfully synthesized via two key stereoselective glycosidation steps. This compound proved to be a highly potent IP3 receptor agonist.

  DOI：

  10.1021/ol0602710

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.
• Design and synthesis of indole derivatives of adenophostin A. A entry into subtype-selective IP3 receptor ligands
  作者：Tetsuya Mochizuki、Akihiko Tanimura、Akihiro Nezu、Mika Ito、Hiroshi Abe、Yoshihiro Ito、Mitsuhiro Arisawa、Satoshi Shuto

  DOI：10.1016/j.tetlet.2009.12.045

  日期：2010.2

  Indole derivatives 3a and 3b of adenophostin A (2) in which the adenine of 2 was replaced with indole or 4-fluoroindole was designed as potential inositol trisphosphate receptor ligands. These target compounds were successfully synthesized from the key disaccharide unit 6. Biological evaluation showed that 3b selectively activates IP(3)R1, a subtype of IP3 receptors. (C) 2009 Elsevier Ltd. All rights reserved.