[9-[(2R,3R,4R,5R)-4-[(2S,3S,4R,5R,6S)-5-acetyloxy-6-methyl-3,4-bis(phenylmethoxy)oxan-2-yl]oxy-3-sulfooxy-5-(sulfooxymethyl)oxolan-2-yl]-6-oxo-3H-purin-2-yl]sulfamic acid | 780023-85-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: [9-[(2R,3R,4R,5R)-4-[(2S,3S,4R,5R,6S)-5-acetyloxy-6-methyl-3,4-bis(phenylmethoxy)oxan-2-yl]oxy-3-sulfooxy-5-(sulfooxymethyl)oxolan-2-yl]-6-oxo-3H-purin-2-yl]sulfamic acid
• CAS: 780023-85-0
• 化学式: C₃₂H₃₇N₅O₁₉S₃
• 分子量: 891.866
• InChiKey: XIBKBGSLCXNHJC-ZTQDMLQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.47
• 重原子数：
  59.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  329.62
• 氢给体数：
  5.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  [9-[(2R,3R,4R,5R)-4-[(2S,3S,4R,5R,6S)-5-acetyloxy-6-methyl-3,4-bis(phenylmethoxy)oxan-2-yl]oxy-3-sulfooxy-5-(sulfooxymethyl)oxolan-2-yl]-6-oxo-3H-purin-2-yl]sulfamic acid 在 palladium dihydroxide 硫酸 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 3'-O-(4''-O-acetyl-α-L-fucopyranosyl)guanosine-2',5'-disulfate
  参考文献：
  名称：

  Structure and Total Synthesis of HF-7, a Neuroactive Glyconucleoside Disulfate from the Funnel-Web Spider Hololena curta

  摘要：

  Spider venom toxins have attracted considerable attention for their ability to block the action of excitatory amino acids such as glutamate and aspartate. A new neuroactive compound designated HF-7 was isolated in 1993 from the venom of a funnel-web spider, Hololena curta. HF-7 was shown to block kainate receptors and, albeit weakly, L-type calcium channels. Spectroscopic analysis established the structure of HF-7 as an unusual acetylated, disulfated fucopyranosyl guanosine, with the acetate ester attached at the 4-position of an alpha-linked fucose ring and two sulfates attached to the ribose ring. Because insufficient quantities of natural HF-7 were available for chemical degradation or X-ray diffraction analysis, total synthesis of three candidate structures was used to establish the identity of HF-7. Once HF-7 was fully characterized as 3'-O-(4 "-O-acetyl-alpha-L-fucopyranosyl)gnanosine-2',5-dusulfate, an improved, targeted synthesis of the natural product was developed.

  DOI：

  10.1021/ja990274q
• 作为产物：
  描述：

  N,N-二苯基-氨基甲酸 2-(乙酰氨基)-9H-嘌呤-6-基酯 在 吡啶 、 ammonium hydroxide 、 pyridine-SO3 complex 、 三氟甲磺酸三甲基硅酯 、 potassium carbonate 、 triethylamine tris(hydrogen fluoride) 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 68.25h， 生成 [9-[(2R,3R,4R,5R)-4-[(2S,3S,4R,5R,6S)-5-acetyloxy-6-methyl-3,4-bis(phenylmethoxy)oxan-2-yl]oxy-3-sulfooxy-5-(sulfooxymethyl)oxolan-2-yl]-6-oxo-3H-purin-2-yl]sulfamic acid
  参考文献：
  名称：

  Structure and Total Synthesis of HF-7, a Neuroactive Glyconucleoside Disulfate from the Funnel-Web Spider Hololena curta

  摘要：

  Spider venom toxins have attracted considerable attention for their ability to block the action of excitatory amino acids such as glutamate and aspartate. A new neuroactive compound designated HF-7 was isolated in 1993 from the venom of a funnel-web spider, Hololena curta. HF-7 was shown to block kainate receptors and, albeit weakly, L-type calcium channels. Spectroscopic analysis established the structure of HF-7 as an unusual acetylated, disulfated fucopyranosyl guanosine, with the acetate ester attached at the 4-position of an alpha-linked fucose ring and two sulfates attached to the ribose ring. Because insufficient quantities of natural HF-7 were available for chemical degradation or X-ray diffraction analysis, total synthesis of three candidate structures was used to establish the identity of HF-7. Once HF-7 was fully characterized as 3'-O-(4 "-O-acetyl-alpha-L-fucopyranosyl)gnanosine-2',5-dusulfate, an improved, targeted synthesis of the natural product was developed.

  DOI：

  10.1021/ja990274q