(2R,3S)-3-Allyloxy-butane-1,2,4-triol | 211630-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-3-Allyloxy-butane-1,2,4-triol
• 英文别名: (2R,3S)-3-prop-2-enoxybutane-1,2,4-triol
• CAS: 211630-38-5
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: IHVRLRBDLXZGPG-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-Allyloxy-butane-1,2,4-triol 在 4-二甲氨基吡啶 、 三氟甲磺酸酐 、 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 73.5h， 生成 (2R,3R,4S,5R,6S)-3,4-Bis-allyloxy-6-((3R,4S)-4-allyloxy-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
• 作为产物：
  描述：

  在 甲醇 、 对甲苯磺酸 作用下， 以50%的产率得到(2R,3S)-3-Allyloxy-butane-1,2,4-triol
  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