5-hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranozyl)-furan-2(5H)-one | 139236-90-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranozyl)-furan-2(5H)-one
• 英文别名: 5-hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)furan-2(5H)-one；5-hydroxy-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)furan-2(5H)-one；furanone glycoside；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(2-hydroxy-5-oxofuran-2-yl)oxolan-2-yl]methyl benzoate
• CAS: 139236-90-1
• 化学式: C₃₀H₂₄O₁₀
• 分子量: 544.515
• InChiKey: NZWNERWLCFLSRE-ZIWDVQFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranozyl)-furan-2(5H)-one 在 盐酸 、 ammonium hydroxide 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 269.0h， 生成 4-(2,3-O-isopropylidene-β-D-ribofuranosyl)quinoline-2-carboxamide
  参考文献：
  名称：

  C-Nucleosides. 23. Synthesis of Enaminone Glycoside and 4-(b-D-Ribofuranosyl)quinoline-2-carboxamide from Furanone Glycoside

  摘要：

  Furanone glycoside (1) was treated with aniline to yield 3-anilino-5-hydroxy-5-(2,3,5-tri-($) under bar O-benzoyl-beta-D-ribofuranosyl)furan-2(5 ($) under bar H)-one (2). Reaction of 2 with trifluoroacetic acid afforded enaminone glycoside (3), whereas treatment of 2 with hydrochloric acid in methanol brought about the ring formation to furnish methyl 4-(2,3,5-tri-($) under bar O-benzoyl-beta-D-ribofuranosyl)quinoline-2-carboxylate (6) together with methyl 2-anilino-4-(3,5-di-($) under bar O-benzoyl-1,4-anhydro-2-deoxy-D-erythropent-1-enofuranosyl)-4-oxobutanoate (4) and methyl 2-anilino-4-(5-benzoyloxymethylfuran-2-yl)-4-oxobutanoate (5) in yields of 12%, 12%, and 7%, respectively. The quinoline ester (6) reacted with aq. ammonia in methanol to produce quinolinecarboxamide ($) under bar C-nucleoside (7).

  DOI：

  10.3987/com-93-6524
• 作为产物：
  描述：

  2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)furan 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 以93%的产率得到5-hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranozyl)-furan-2(5H)-one
  参考文献：
  名称：

  C-Nucleosides. 6. Synthesis of 5-methoxy-5-(2,3,5-tri-O-benzoyl-.beta.-D-ribofuranosyl)furan-2(5H)-one and its ring transformation

  摘要：

  DOI：

  10.1021/jo00229a017

文献信息

• Ito, Yasutaka; Wakimura, Masakazu; Ito, Chihiro, Heterocycles, 1992, vol. 34, # 11, p. 2131 - 2136
  作者：Ito, Yasutaka、Wakimura, Masakazu、Ito, Chihiro、Maeba, Isamu

  DOI：——

  日期：——
• C-Nucleosides. 22. Synthesis of Quinoxaline Acyclo-C-nucleoside
  作者：Isamu Maeba、Masakazu Wakimura、Yasutaka Ito、Chihiro Ito

  DOI：10.3987/com-93-6501

  日期：——

  The synthesis of quinoxaline acyclo-C-nucleoside, 2-[(3S)-3,4-dihydroxybutyl]3-methylquinoxaline (6), is described. Treatment of furanone glycoside (1) with 1,2-diaminobenze gave a mixture of Z- and E-3-[2-[4-0-benzoyl-(3S)-3-hydroxy-1-butenyl]-3-quinoxalinylmethyl]-1,2,3,4-tetrahydroquinoxalin-2-ones (2a and 2b). Compound (2a) was treated with acetic acid to give three products, Z- and E-(3S)-3-hydroxy-1-butenyl]-3-methylquinoxalines (3a and 3b) and quinoxalin-2-one (4). Catalytic hydrogenation of 3a,b produced 2-[4-0-benzoyl-(3S)-3-hydroxybutyl]-3-methylquinoxaline (5). Removal of the protecting group in 5 afforded compound (6).
• 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).
• Ito, Yasutaka; Wakimura, Masakazu; Ito, C., Heterocycles, 1992, vol. 34, # 5, p. 955 - 964
  作者：Ito, Yasutaka、Wakimura, Masakazu、Ito, C.、Meaba, Isamu

  DOI：——

  日期：——
• MAEBA, ISAMU;IIJIMA, TAKASHI;MATSUDA, YOKO;ITO, CHIHIRO, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 73-76
  作者：MAEBA, ISAMU、IIJIMA, TAKASHI、MATSUDA, YOKO、ITO, CHIHIRO

  DOI：——

  日期：——