[2'-O-acetyl-3'-O-(3",4"-di-O-acetyl-2",6"-di-O-benzyl-α-D-glucopyranosyl)-5'-O-benzyl-β-D-ribofuranosyloxy]prop-3-yne | 197644-84-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2'-O-acetyl-3'-O-(3",4"-di-O-acetyl-2",6"-di-O-benzyl-α-D-glucopyranosyl)-5'-O-benzyl-β-D-ribofuranosyloxy]prop-3-yne
• 英文别名: Bn(-2)[Bn(-6)]Glc3Ac4Ac(a1-3)[Bn(-5)]Ribf2Ac(b)-O-prop-2-ynyl；[(2R,3R,4S,5R,6R)-4-acetyloxy-6-[(2R,3R,4R,5R)-4-acetyloxy-2-(phenylmethoxymethyl)-5-prop-2-ynoxyoxolan-3-yl]oxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 197644-84-1
• 化学式: C₄₁H₄₆O₁₃
• 分子量: 746.808
• InChiKey: YKWZJVLAURRHGT-QBFSEAGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  54
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [2'-O-acetyl-3'-O-(3",4"-di-O-acetyl-2",6"-di-O-benzyl-α-D-glucopyranosyl)-5'-O-benzyl-β-D-ribofuranosyloxy]prop-3-yne 在 甲醇 、 sodium methylate 作用下， 反应 1.5h， 生成 (2R,3S,4S,5R,6R)-5-Benzyloxy-2-benzyloxymethyl-6-((2R,3S,4R,5R)-2-benzyloxymethyl-4-hydroxy-5-prop-2-ynyloxy-tetrahydro-furan-3-yloxy)-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Synthesis of Potent Agonists of the d-myo-Inositol 1,4,5-Trisphosphate Receptor Based on Clustered Disaccharide Polyphosphate Analogues of Adenophostin A

  摘要：

  Clustered disaccharide analogues of adenophostin A (2), i.e. mono-, di-, and tetravalent derivatives 6-8, respectively, were synthesized and evaluated as novel ligands for the tetrameric D-myo-inositol 1,4,5-trisphosphate receptor (IP3R). The synthesis was accomplished via Sonogashira coupling of propargyl 2-O-acetyl-5-O-benzyl-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-alpha-D-glucopyranosyl)-beta-D-ribofuranoside (16) with iodobenzene 18, 22, or 25, followed by deacetylation, phosphorylation, and deprotection. The abilities of the target compounds 6-8, as well as ribophostin 4, propylphostin 5, and IP3 (1), to evoke Ca2+ release from permeabilized hepatocytes or displacement of [H-3]IP3 from its receptor in hepatic membranes were compared. Although the binding affinities of 4-8 were similar, there were modest though significant differences in their potencies in Ca2+ release assays: tetraphostin 8 > IP3 similar to diphostin 7 > phenylphostin 6 > ribophostin 4 similar to propylphostin 5.

  DOI：

  10.1021/jm000957c
• 作为产物：
  描述：

  2-丙炔-1-醇 、 1,2,3',4'-Tetra-O-acetyl-2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-D-ribofuranose 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以81%的产率得到[2'-O-acetyl-3'-O-(3",4"-di-O-acetyl-2",6"-di-O-benzyl-α-D-glucopyranosyl)-5'-O-benzyl-β-D-ribofuranosyloxy]prop-3-yne
  参考文献：
  名称：

  腺苷A簇状二糖多磷酸酯类似物的合成

  摘要：

  通过炔丙基2 - O-乙酰基-5- O-苄基-3- O-（3,4-二-O-乙酰基- ）的Sonogashira偶联，制备了IP 3受体的三个新的潜在配体（即化合物5-7）。2,6-二-O-苄基-α-d-吡喃葡萄糖基）-β-d-呋喃核糖苷（15）与碘苯，1,2-二碘苯和1,2,4,5-四碘苯，然后进行脱乙酰基化，磷酸化和脱保护。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)01811-x