6-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranosyl fluoride | 211630-26-1

• 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: 6-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranosyl fluoride
• 英文别名: [(2R,3R,4S,5R)-6-fluoro-5-phenylmethoxy-3,4-bis(prop-2-enoxy)oxan-2-yl]methyl acetate
• CAS: 211630-26-1
• 化学式: C₂₁H₂₇FO₆
• 分子量: 394.44
• InChiKey: WYADZCXOXGMKHU-AWGDKMGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranosyl fluoride 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (2R,3R,4S,5R,6R)-3,4-Bis-allyloxy-6-((2R,3S,4S)-4-allyloxy-2-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
• 作为产物：
  描述：

  1,6-di-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranose 在 哌啶 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 6-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranosyl fluoride
  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 1-0-[(3S,4R)-3-hydroxytetrahydrofuran-4-yl]-α-D-glucopyranoside 3,4,3′-trisphosphate as a novel potent IP3 receptor ligand
  作者：Kazuya Tatani、Satoshi Shuto、Yoshihito Ueno、Akira Matsuda

  DOI：10.1016/s0040-4039(98)00954-x

  日期：1998.7

  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.