(2"S,3"S)-5-O-benzyl-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2",3"-dimethoxybutane-2",3"-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranoside | 197644-82-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2"S,3"S)-5-O-benzyl-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2",3"-dimethoxybutane-2",3"-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranoside
• 英文别名: 5-O-benzyl-3-O-{2',6'-di-O-benzyl-3',4'-di-O-[(2''S,3''S)-2'',3''-dimethoxybutane-2'',3''-diyl]-α-D-glucopyranosyl}-1,2-O-isopropylidene-α-D-ribofuranoside；(2S,3S,4aR,5R,7R,8R,8aS)-7-[[(3aR,5R,6R,6aR)-2,2-dimethyl-5-(phenylmethoxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]-2,3-dimethoxy-2,3-dimethyl-8-phenylmethoxy-5-(phenylmethoxymethyl)-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine
• CAS: 197644-82-9
• 化学式: C₄₁H₅₂O₁₂
• 分子量: 736.857
• InChiKey: HJVQAHGAYKQGEQ-BFCOFURYSA-N

物化性质

• 熔点：
  93-94 °C
• 沸点：
  760.3±60.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2"S,3"S)-5-O-benzyl-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2",3"-dimethoxybutane-2",3"-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranoside 在 吡啶 、 水 、 溶剂黄146 作用下， 以 乙二醇 为溶剂， 反应 17.25h， 生成 1,2,3',4'-Tetra-O-acetyl-2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-D-ribofuranose
  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：

  ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 甲醇 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 (2"S,3"S)-5-O-benzyl-3-O-[2',6'-di-O-benzyl-3',4'-di-O-(2",3"-dimethoxybutane-2",3"-diyl)-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranoside
  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

文献信息

• Synthesis of Clustered Disaccharide Polyphosphate Analogues of Adenophostin A
  作者：Martin de Kort、A.Rob P.M. Valentijn、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/s0040-4039(97)01811-x

  日期：1997.10

  Three new potential ligands for the IP3 receptor (i.e. compounds 5–7) were prepared by Sonogashira coupling of propargyl 2-O-acetyl-5-O-benzyl-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-d- glycopyranosyl)-β-d-ribofuranoside (15) with iodobenzene, 1,2-diiodobenzene and 1,2,4,5-tetraiodobenzene, followed by deacetylation, phosphorylation and deprotection. © 1997 Elsevier Science Ltd.

  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。
• Synthesis of Photoaffinity Derivatives of Adenophostin A
  作者：Martin de Kort、Jaco Luijendijk、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1002/1099-0690(200009)2000:17<3085::aid-ejoc3085>3.0.co;2-a

  日期：2000.9