Z-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-3-(4-hydroxy)anilino-2-propen-1-one | 164666-91-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Z-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-3-(4-hydroxy)anilino-2-propen-1-one
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-[(Z)-3-(4-hydroxyanilino)prop-2-enoyl]oxolan-2-yl]methyl benzoate
• CAS: 164666-91-5
• 化学式: C₃₅H₂₉NO₉
• 分子量: 607.617
• InChiKey: IPVGEUWHPDYZFD-CXXQGHQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Z-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-3-(4-hydroxy)anilino-2-propen-1-one 在 盐酸羟胺 、 sodium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 6.5h， 生成 5-(β-D-ribofuranosyl)isoxazole
  参考文献：
  名称：

  C-Nucleosides. 21. Synthesis of Isoxazole C-Nucleoside from Furanone Glycoside via Enaminone Glycoside

  摘要：

  Synthesis of the versatile and stable C-nucleoside precursor enaminone glycosides (3a,b) was achieved by reaction of furanone glycoside (1) with 2- and 4-aminophenols. Treatment of enaminone (3b) with hydroxylamine hydrochloride yielded 5-hydroxy-4,5-dihydroisoxazole(5), which on dehydration with toluene-p-sulfonic acid in benzene gave 5-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)isoxazole (6). Deblocking of compound (6) with sodium carbonate gave 5-(beta-D-ribofuranosyl)isoxazole (7).

  DOI：

  10.3987/com-93-6370
• 作为产物：
  描述：

  对氨基苯酚 、 5-hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranozyl)-furan-2(5H)-one 以 氯仿 为溶剂， 反应 7.0h， 以54.1%的产率得到Z-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-3-(4-hydroxy)anilino-2-propen-1-one
  参考文献：
  名称：

  C-Nucleosides. 21. Synthesis of Isoxazole C-Nucleoside from Furanone Glycoside via Enaminone Glycoside

  摘要：

  Synthesis of the versatile and stable C-nucleoside precursor enaminone glycosides (3a,b) was achieved by reaction of furanone glycoside (1) with 2- and 4-aminophenols. Treatment of enaminone (3b) with hydroxylamine hydrochloride yielded 5-hydroxy-4,5-dihydroisoxazole(5), which on dehydration with toluene-p-sulfonic acid in benzene gave 5-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)isoxazole (6). Deblocking of compound (6) with sodium carbonate gave 5-(beta-D-ribofuranosyl)isoxazole (7).

  DOI：

  10.3987/com-93-6370

文献信息

• Synthesis of 3-β-d-ribofuranosyl-1 H-pyrazole-4-carboxamide
  作者：Yasufumi Nishiyama、Natsu Nishimura、Naoko Kuroyanagi、Isamu Maeba

  DOI：10.1016/s0008-6215(97)00047-5

  日期：1997.5

  Abstract The synthesis of 3-β- d -ribofuranosyl-1 H -pyrazole-4-carboxamide ( 11 ) is described. Treatment of enaminone glycoside 1 with trimethyl orthoformate afforded the aldehyde 2 . The aldehyde 2 was oximated with hydroxylamine. Oxime 3 was cyclized with hydrazine to afford the pyrazole 8 . The pyrazole 8 was dehydrated with acetic anhydride, and the nitrile 9 was treated with nickel acetate in acetic

  摘要描述了3-β-d-呋喃呋喃糖基-1 H-吡唑-4-羧酰胺（11）的合成。用原甲酸三甲酯处理烯胺酮糖苷1得到醛2。醛2用羟胺肟化。用肼使肟3环化，得到吡唑8。吡唑8用乙酸酐脱水，腈9用乙酸镍的乙酸溶液处理。将所得的羧酰胺10用氨水解封闭，得到11。
• Synthesis of 3-β-d-ribofuranosylpyrazole-1-carboxamide
  作者：Natsu Nishimura、Masashi Banno、Ayumi Maki、Yasufumi Nishiyama、Isamu Maeba

  DOI：10.1016/s0008-6215(97)10111-2

  日期：1998.2

  Abstract The synthesis of 3-β- d -ribofuranosylpyrazole-1-carboxamide (12) is described. Treatment of glycosyl enaminone 4 with semicarbazide hydrochloride in dioxane afforded three cyclocondensation products, 5-(2,3,5-tri-O-benzoyl-β- d -ribofuranosyl)pyrazole-1-carboxamide (5), 3-(2,3,5-tri-O-benzoyl-β- d -ribofuranosyl)pyrazole-1-carboxamide (6), and 3(5)-(2,3,5-tri-O-benzoyl-β- d -ribofuranosyl)pyrazole

  摘要描述了3-β-d-呋喃核糖基吡唑-1-羧酰胺（12）的合成。在二恶烷中用氨基脲盐酸盐处理糖基烯氨基酮4得到三种环缩合产物，5-（2,3,5-三-O-苯甲酰基-β-d-核呋喃糖基）吡唑-1-羧酰胺（5），3-（2， 3,5-三-O-苯甲酰基-β-d-呋喃呋喃糖基）吡唑-1-羧酰胺（6）和3（5）-（2,3,5-三-O-苯甲酰基-β-d-呋喃呋喃糖基）吡唑（7）的收率分别为51％，5％和16％。由于消除了氨基甲酰基，化合物5在室温下逐渐转化为7。在室温下用盐酸在甲醇中处理4，得到90的3,3-二甲氧基-1-（2,3,5-三-O-苯甲酰基-β-d-核呋喃糖基）丙烷-1-酮（9） ％ 屈服。用氨基脲处理9，得到相应的氨基脲10，
• C-Nucleosides. 24. Synthesis of Pyrazolo[1,5-a]pyrimidine C-Nucleoside through Cyclocondensation of Enaminone Glycoside with Aminopyrazoles
  作者：Isamu Maeba、Yasufumi Nishiyama、Shigeyuki Kanazawa、Akiko Sato

  DOI：10.3987/com-94-6972

  日期：——

  A versatile intermediate enaminone glycoside (1) for C-nucleoside synthesis was treated with aminopyrazoles to give pyrazolo[1,5-a]pyrimidine C-nucleosides.
• C-Nucleosides. 21. Synthesis of Isoxazole C-Nucleoside from Furanone Glycoside via Enaminone Glycoside
  作者：Isamu Maeba、Yasutaka Ito、Masakazu Wakimura、Chihiro Ito

  DOI：10.3987/com-93-6370

  日期：——

  Synthesis of the versatile and stable C-nucleoside precursor enaminone glycosides (3a,b) was achieved by reaction of furanone glycoside (1) with 2- and 4-aminophenols. Treatment of enaminone (3b) with hydroxylamine hydrochloride yielded 5-hydroxy-4,5-dihydroisoxazole(5), which on dehydration with toluene-p-sulfonic acid in benzene gave 5-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)isoxazole (6). Deblocking of compound (6) with sodium carbonate gave 5-(beta-D-ribofuranosyl)isoxazole (7).