Carbonic acid (2R,3R,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester tert-butyl ester | 228394-71-6

• 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: Carbonic acid (2R,3R,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester tert-butyl ester
• CAS: 228394-71-6
• 化学式: C₃₅H₅₅N₅O₉Si₂
• 分子量: 746.021
• InChiKey: NBNHGQSWOXDZGP-CTDWIVFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  51.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  165.12
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Carbonic acid (2R,3R,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester tert-butyl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以60%的产率得到
  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：

  鸟苷 在 咪唑 、 4-二甲氨基吡啶 、 18-冠醚-6 、 potassium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 Carbonic acid (2R,3R,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester tert-butyl ester
  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