ethyl 2-methyl-5-(4-thio-β-D-erythrofuranosyl)furan-3-carboxylate | 109200-68-2

• 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 2-methyl-5-(4-thio-β-D-erythrofuranosyl)furan-3-carboxylate
• 英文别名: 3-ethoxycarbonyl-2-methyl-5-(4-thio-β-D-erythrofuranosyl)furan；ethyl 5-[(2R,3R,4S)-3,4-dihydroxythiolan-2-yl]-2-methylfuran-3-carboxylate
• CAS: 109200-68-2
• 化学式: C₁₂H₁₆O₅S
• 分子量: 272.322
• InChiKey: LBTJUHTVFWSJHU-IEBDPFPHSA-N

物化性质

• 沸点：
  422.5±45.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-5-(4-thio-β-D-erythrofuranosyl)furan-3-carboxylate 在 间氯过氧苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.33h， 生成 ethyl 2-methyl-5-(4-thio-β-D-erythrofuranosyl)furan-3-carboxylate S-[(R)-oxide] 、 ethyl 2-methyl-5-(4-thio-β-D-erythrofuranosyl)furan-3-carboxylate S-[(S)-oxide]
  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 盐酸 、 叔丁基硫醇 作用下， 反应 20.17h， 生成 ethyl 2-methyl-5-(4-thio-β-D-erythrofuranosyl)furan-3-carboxylate
  参考文献：
  名称：

  Use of 2-methyl-2-propanethiol in the synthesis of C-thioglycosyl derivatives

  摘要：

  DOI：

  10.1016/s0008-6215(00)90141-1

文献信息

• Use of 2-methyl-2-propanethiol in the synthesis of C-thioglycosyl derivatives
  作者：F.J. Lopez Aparicio、F. Zorrilla Benitez、F. Santoyo Gonzalez、J.L. Asensio Rosell

  DOI：10.1016/s0008-6215(00)90141-1

  日期：1986.11
• 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.