Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3S,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester | 228394-67-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3S,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester
• 英文别名: [(2S,3R,4R,5S,6S)-6-[(2R,3S,4R,5R)-4-hydroxy-2-(hydroxymethyl)-5-[6-oxo-2-(phenylmethoxycarbonylamino)-1H-purin-9-yl]oxolan-3-yl]oxy-2-methyl-4,5-bis(phenylmethoxy)oxan-3-yl] acetate
• CAS: 228394-67-0
• 化学式: C₄₀H₄₃N₅O₁₂
• 分子量: 785.808
• InChiKey: CCLWDTQGWNMXSO-GQOGBTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  211
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3S,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester 在 三氧化硫 作用下， 反应 2.0h， 以99%的产率得到Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-sulfooxy-2-sulfooxymethyl-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl 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
• 作为产物：
  描述：

  {9-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid benzyl ester 在 咪唑 、 四丁基氟化铵 、 zinc dibromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3S,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl 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