5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-isoxazole-4-carbaldehyde | 191472-11-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-isoxazole-4-carbaldehyde
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(4-formyl-1,2-oxazol-5-yl)oxolan-2-yl]methyl benzoate
• CAS: 191472-11-4
• 化学式: C₃₀H₂₃NO₉
• 分子量: 541.514
• InChiKey: XCSWENCLXHSJIX-ZRIRBKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-isoxazole-4-carbaldehyde 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 530.0h， 生成 3-cyano-7-methoxy-4-(β-D-ribofuranosyl)-1H-1,5-benzodiazepine
  参考文献：
  名称：

  Novel ring transformation of 5-(2,3,5-tri-O-benzoyl-β-d-ribofuranosyl)isoxazole-4-carbaldehyde with 1,2-diaminobenzenes to 3-cyano-1,5-benzodiazepine C-nucleosides

  摘要：

  Syntheses of 3-cyano-7- and 8-substituted-4-(beta -D-ribofuranosyl)-1H-1,5-benzodiazepines were reported. Treatment of isoxazole carbaldehyde with 1,2-diamino-4-nitrobenzene in chloroform gave a Schiffs base, 4-(2-amino-5-nitrophenyl)iminomethyl-5-(2,3,5-tri-O-benzoyl-beta -D-ribofuranosyl)isoxazole in 82% yield with no trace of the other regioisomer. The cyclocondensation of the resulting Schiffs base in benzene containing trifluoroacetic acid (TFA) gave 3-cyano-8-nitro-4-(2,3,5-tri-O-benzoyl-beta -D-rbofuranosyl)-1H-1,5-benzodiazepine in 49% yield. The same reac tion of isoxazole carbaldeyde with 1,2-diamino-4-methoxy- and 4-chlorobenzenes afforded the corresponding Schiffs bases. Extending the reaction time for Schiff's base gave the corresponding cyanobenzodiazepines in good yields. Debenzoylation of the compounds with sodium methoxide produced deprotected C-nucleosides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00231-7
• 作为产物：
  描述：

  1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-3-(4-hydroxy)anilino-1-oxo-2-propene-2-carbaldehyde 在 hydroxylamine-O-sulfonic acid 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以11%的产率得到1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-3-(4-hydroxy)anilino-1-oxo-2-propene-2-carbonitrile
  参考文献：
  名称：

  3-β-d-呋喃呋喃糖基-1 H-吡唑-4-羧酰胺的合成

  摘要：

  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。

  DOI：

  10.1016/s0008-6215(97)00047-5

文献信息

• Nishimura, Natsu; Koyano, Yuko; Sugiura, Mitchiharu, Heterocycles, 1999, vol. 51, # 4, p. 803 - 809
  作者：Nishimura, Natsu、Koyano, Yuko、Sugiura, Mitchiharu、Maeba, Isamu

  DOI：——

  日期：——
• 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。
• Novel ring transformation of 5-(2,3,5-tri-O-benzoyl-β-d-ribofuranosyl)isoxazole-4-carbaldehyde with 1,2-diaminobenzenes to 3-cyano-1,5-benzodiazepine C-nucleosides
  作者：Natsu Nishimura、Haruna Hisamitsu、Michiharu Sugiura、Isamu Maeba

  DOI：10.1016/s0008-6215(00)00231-7

  日期：2000.11

  Syntheses of 3-cyano-7- and 8-substituted-4-(beta -D-ribofuranosyl)-1H-1,5-benzodiazepines were reported. Treatment of isoxazole carbaldehyde with 1,2-diamino-4-nitrobenzene in chloroform gave a Schiffs base, 4-(2-amino-5-nitrophenyl)iminomethyl-5-(2,3,5-tri-O-benzoyl-beta -D-ribofuranosyl)isoxazole in 82% yield with no trace of the other regioisomer. The cyclocondensation of the resulting Schiffs base in benzene containing trifluoroacetic acid (TFA) gave 3-cyano-8-nitro-4-(2,3,5-tri-O-benzoyl-beta -D-rbofuranosyl)-1H-1,5-benzodiazepine in 49% yield. The same reac tion of isoxazole carbaldeyde with 1,2-diamino-4-methoxy- and 4-chlorobenzenes afforded the corresponding Schiffs bases. Extending the reaction time for Schiff's base gave the corresponding cyanobenzodiazepines in good yields. Debenzoylation of the compounds with sodium methoxide produced deprotected C-nucleosides. (C) 2000 Elsevier Science Ltd. All rights reserved.