ethyl 5-(4-S-acetyl-4-thio-D-arabino-tetritol-1-yl)-2-methylfuran-3-carboxylate | 572917-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 5-(4-S-acetyl-4-thio-D-arabino-tetritol-1-yl)-2-methylfuran-3-carboxylate
• 英文别名: ethyl 5-[(1S,2S,3S)-4-acetylsulfanyl-1,2,3-trihydroxybutyl]-2-methylfuran-3-carboxylate
• CAS: 572917-84-1
• 化学式: C₁₄H₂₀O₇S
• 分子量: 332.375
• InChiKey: WWWBJOOMILMJSB-RAIGVLPGSA-N

物化性质

• 沸点：
  534.3±50.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-S-acetyl-4-thio-D-arabino-tetritol-1-yl)-2-methylfuran-3-carboxylate 在 三氟乙酸 作用下， 以 硝基甲烷 、 乙醇 、 水 为溶剂， 反应 3.0h， 生成 (1S,2S,3R,4S)-2-[4-(ethoxycarbonyl)-5-methylfuran-2-yl]-3,4-dihydroxy-1-methylthiolanium triflate
  参考文献：
  名称：

  Synthesis of furan 4′-thio-C-nucleosides, their methylsulfonium and sulfoxide derivatives. Evaluation as glycosidase inhibitors

  摘要：

  A series of furan C-nucleosides having a sulfur atom in the sugar ring were synthesised. The alpha and beta anomers of 3-ethoxycarbonyl-2-methyl-5-(4'-thin-D-erythrofuranosyl)furans 10 and 11 were obtained by acid treatment of (4'-S-acetyl-4'-thin-D-arabino-tetritol-1-yl)furan 9. Oxidation of 10 with m-chloroperbenzoic acid gave sulfoxide 12 as one epimer at the sulfur atom whereas 11 was transformed into sulfoxide 13 as an epimeric mixture. S-Methylation of 10 and 11 with methyl triflate led to sulfonium salts 14 and 15. The prepared compounds were found to be moderate inhibitors of alpha-L-fucosidase. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00339-9
• 作为产物：
  描述：

  ethyl 2-methyl-5-(D-arabino-tetritol-1-yl)furan-3-carboxylate 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 ethyl 5-(4-S-acetyl-4-thio-D-arabino-tetritol-1-yl)-2-methylfuran-3-carboxylate
  参考文献：
  名称：

  Synthesis of furan 4′-thio-C-nucleosides, their methylsulfonium and sulfoxide derivatives. Evaluation as glycosidase inhibitors

  摘要：

  A series of furan C-nucleosides having a sulfur atom in the sugar ring were synthesised. The alpha and beta anomers of 3-ethoxycarbonyl-2-methyl-5-(4'-thin-D-erythrofuranosyl)furans 10 and 11 were obtained by acid treatment of (4'-S-acetyl-4'-thin-D-arabino-tetritol-1-yl)furan 9. Oxidation of 10 with m-chloroperbenzoic acid gave sulfoxide 12 as one epimer at the sulfur atom whereas 11 was transformed into sulfoxide 13 as an epimeric mixture. S-Methylation of 10 and 11 with methyl triflate led to sulfonium salts 14 and 15. The prepared compounds were found to be moderate inhibitors of alpha-L-fucosidase. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00339-9

文献信息

• Synthesis of furan 4′-thio-C-nucleosides, their methylsulfonium and sulfoxide derivatives. Evaluation as glycosidase inhibitors
  作者：Vı́ctor Ulgar、Óscar López、Inés Maya、José G Fernández-Bolaños、Mikael Bols

  DOI：10.1016/s0040-4020(03)00339-9

  日期：2003.4

  A series of furan C-nucleosides having a sulfur atom in the sugar ring were synthesised. The alpha and beta anomers of 3-ethoxycarbonyl-2-methyl-5-(4'-thin-D-erythrofuranosyl)furans 10 and 11 were obtained by acid treatment of (4'-S-acetyl-4'-thin-D-arabino-tetritol-1-yl)furan 9. Oxidation of 10 with m-chloroperbenzoic acid gave sulfoxide 12 as one epimer at the sulfur atom whereas 11 was transformed into sulfoxide 13 as an epimeric mixture. S-Methylation of 10 and 11 with methyl triflate led to sulfonium salts 14 and 15. The prepared compounds were found to be moderate inhibitors of alpha-L-fucosidase. (C) 2003 Elsevier Science Ltd. All rights reserved.