2-amino-9-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-[(2S,3S,4R,5R,6S)-5-hydroxy-6-methyl-3,4-bis(phenylmethoxy)oxan-2-yl]oxyoxolan-2-yl]-1H-purin-6-one | 1053268-76-0

• 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: 2-amino-9-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-[(2S,3S,4R,5R,6S)-5-hydroxy-6-methyl-3,4-bis(phenylmethoxy)oxan-2-yl]oxyoxolan-2-yl]-1H-purin-6-one
• CAS: 1053268-76-0
• 化学式: C₃₀H₃₅N₅O₉
• 分子量: 609.636
• InChiKey: IYALXDQQXLPJNE-CPHJONKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  192
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-amino-9-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-[(2S,3S,4R,5R,6S)-5-hydroxy-6-methyl-3,4-bis(phenylmethoxy)oxan-2-yl]oxyoxolan-2-yl]-1H-purin-6-one 在 吡啶 、 pyridine-SO3 complex 、 硫酸 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 44.0h， 生成 Bn(-2)[Bn(-3)]Fuc4Ac(a1-3)Ribf2S5S(b)-guanin-9-yl
  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 、 三氟甲磺酸三甲基硅酯 、 triethylamine tris(hydrogen fluoride) 作用下， 以 甲醇 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 36.25h， 生成 2-amino-9-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-[(2S,3S,4R,5R,6S)-5-hydroxy-6-methyl-3,4-bis(phenylmethoxy)oxan-2-yl]oxyoxolan-2-yl]-1H-purin-6-one
  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

文献信息

• Structure and Total Synthesis of HF-7, a Neuroactive Glyconucleoside Disulfate from the Funnel-Web Spider <i>Hololena curta</i>
  作者：Jinping McCormick、Yingbo Li、Kevin McCormick、Howard I. Duynstee、Anke K. van Engen、Gijs A. van der Marel、Bruce Ganem、Jacques H. van Boom、Jerrold Meinwald

  DOI：10.1021/ja990274q

  日期：1999.6.1

  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.