1,6-di-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranose | 211630-34-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-di-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranose
• CAS: 211630-34-1
• 化学式: C₂₃H₃₀O₈
• 分子量: 434.486
• InChiKey: WJCZPPMGRKBZFZ-HZQGQDIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,6-di-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranose 在 哌啶 、 三氟甲磺酸三甲基硅酯 、 三乙胺 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 Acetic acid (2R,3R,4S,5R)-3,4-bis-allyloxy-6-((2R,3S,4S)-4-allyloxy-2-benzyloxymethyl-tetrahydro-furan-3-yloxy)-5-benzyloxy-tetrahydro-pyran-2-ylmethyl 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 、 methyl 3,4-di-O-allyl-2,6-di-O-benzyl-α-D-glucopyranoside 在 硫酸 作用下， 以79%的产率得到1,6-di-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranose
  参考文献：
  名称：

  Synthesis of 1-0-[(3S,4R)-3-hydroxytetrahydrofuran-4-yl]-α-D-glucopyranoside 3,4,3′-trisphosphate as a novel potent IP3 receptor ligand

  摘要：

  1-O-[(3S,4R)-3-Hydroxytetrahydrofuran-4-yl]-alpha-D-glucopyranoside 3,4,3'-trisphosphate (5) was designed and synthesized as a novel IP3 receptor ligand. This compound bound strongly to IP3 receptor from porcine cerebella with an affinity comparable to that of IP3. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00954-x