3-O-allyl-1,4-anhydro-5-O-benzyl-D-ribitol | 219530-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-O-allyl-1,4-anhydro-5-O-benzyl-D-ribitol
• 英文别名: (3S,4S,5R)-5-(phenylmethoxymethyl)-4-prop-2-enoxyoxolan-3-ol
• CAS: 219530-20-8
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: LYMGKFUOVUNUDT-ZNMIVQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-O-allyl-1,4-anhydro-5-O-benzyl-D-ribitol 在 palladium on activated charcoal 四氮唑 、 三氟甲磺酸三甲基硅酯 、 WK-20 resin column (Na⁺ form) 、 氢气 、 对甲苯磺酸 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 37.7h， 生成 (2R,3R,4S)-3-hydroxy-2-(hydroxymethyl)tetrahydrofuran-4-yl α-D-glucopyranoside 3,4,3'-trisphosphate hexasodium salt
  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 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 67.5h， 生成 3-O-allyl-1,4-anhydro-5-O-benzyl-D-ribitol
  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

文献信息

• Synthesis of Adenophostin Analogues Lacking the Adenine Moiety as Novel Potent IP₃ Receptor Ligands:  Some Structural Requirements for the Significant Activity of Adenophostin A
  作者：Satoshi Shuto、Kazuya Tatani、Yoshihito Ueno、Akira Matsuda

  DOI：10.1021/jo980925l

  日期：1998.11.1

  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.
• An Efficient One-Stage Deprotection/Reduction of 1,2-<i>O</i>-Isopropylidene Furanoses to the Corresponding Tetrahydrofurans
  作者：Gregory J. Ewing、Morris J. Robins

  DOI：10.1021/ol9901117

  日期：1999.8.1

  Treatment of 1,2-O-isopropylidenefuranose derivatives with triethylsilane/boron trifluoride etherate results in generation of the corresponding tetrahydrofurans. This one stage process removes the 1,2 O-isopropylidene group with accompanying deoxygenation at the anomeric position and is compatible with several hydroxyl protecting groups.