(2R,3R,4S,5R,6S)-3,4-Bis-allyloxy-6-((3S,4R,5R)-4-allyloxy-5-benzyloxymethyl-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran | 219530-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-3,4-Bis-allyloxy-6-((3S,4R,5R)-4-allyloxy-5-benzyloxymethyl-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran
• 英文别名: (2R,3R,4S,5R,6S)-5-phenylmethoxy-2-(phenylmethoxymethyl)-6-[(3S,4R,5R)-5-(phenylmethoxymethyl)-4-prop-2-enoxyoxolan-3-yl]oxy-3,4-bis(prop-2-enoxy)oxane
• CAS: 219530-55-9
• 化学式: C₄₁H₅₀O₉
• 分子量: 686.843
• InChiKey: SJONTMBJLOCYMT-SMNOHNTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  50
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-3,4-Bis-allyloxy-6-((3S,4R,5R)-4-allyloxy-5-benzyloxymethyl-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran 在 palladium on activated charcoal 四氮唑 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 Phosphoric acid dibenzyl ester (2R,3R,4R,5R,6S)-5-benzyloxy-2-benzyloxymethyl-6-[(3S,4R,5R)-5-benzyloxymethyl-4-(bis-benzyloxy-phosphoryloxy)-tetrahydro-furan-3-yloxy]-4-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-3-yl 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：

  3-O-allyl-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose 在 盐酸 、 sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 68.2h， 生成 (2R,3R,4S,5R,6S)-3,4-Bis-allyloxy-6-((3S,4R,5R)-4-allyloxy-5-benzyloxymethyl-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran
  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