diethyl (2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylate | 388110-10-9

• 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: diethyl (2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylate
• 英文别名: diethyl (2S,3R)-3-hydroxy-5-oxooxolane-2,3-dicarboxylate
• CAS: 388110-10-9
• 化学式: C₁₀H₁₄O₇
• 分子量: 246.217
• InChiKey: JLPBCOZEBZAKOS-GMSGAONNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 diethyl (2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylate 在 三氯氧磷 作用下， 以 吡啶 、 甲醇 、 乙醚 为溶剂， 反应 2.0h， 生成 diethyl 3-methoxy-2(5H)-furanone-4,5-dicarboxylate
  参考文献：
  名称：

  Analogues of the Quararibea metabolite chiral enolic-γ-lactone from (2S,3S)- and (2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acids

  摘要：

  Reaction of dialkyl (2S,3S)- or (2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylates with POCl3 in pyridine followed by diazomethane resulted in the isolation of dialkyl 2S-4-methoxy-5-oxo-2,5-dihydro-2,3-furandicarboxylates, which are analogues of the Quararibea metabolite chiral enolic-gamma-lactone (3-hydroxy-4,5-(R)-dimethyl-2(5H)-furanone). An unusual alpha-hydroxylation of gamma-butyrolactone takes place involving POCl3 in pyridine. When the dehydration was facilitated with methanesulfonyl chloride in triethylamine, instead of POCl3, aromatic dialkyl 5-[(methylsulfonyl)oxy]-2,3-furandicarboxylates were obtained. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.133
• 作为产物：
  描述：

  乙醇 、 disodium (2S,3R)‑tetrahydro‑3‑hydroxy‑5‑oxo‑2,3‑furandicarboxylate 在 氯化亚砜 作用下， 反应 48.0h， 以68%的产率得到diethyl (2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylate
  参考文献：
  名称：

  Chiral γ-butyrolactones related to optically active 2-hydroxycitric acids

  摘要：

  The complete spectroscopic data and other physical constants of two naturally occuring, diastereomeric, optically active gamma-lactones derived from inexpensive 2-hydroxycitric acids, namely garcinia acid [(2S,35)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid] and hibiscus acid [(2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid] and related derivatives have been described for the first time. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00431-3

文献信息

• Chiral γ-butyrolactones related to optically active 2-hydroxycitric acids
  作者：Ibrahim Ibnusaud、Puthiaparambil Tom Thomas、Rajasekharan Nair Rani、Paleapadam Vavan Sasi、Thomas Beena、Abdulkhader Hisham

  DOI：10.1016/s0040-4020(02)00431-3

  日期：2002.6

  The complete spectroscopic data and other physical constants of two naturally occuring, diastereomeric, optically active gamma-lactones derived from inexpensive 2-hydroxycitric acids, namely garcinia acid [(2S,35)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid] and hibiscus acid [(2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid] and related derivatives have been described for the first time. (C) 2002 Published by Elsevier Science Ltd.
• Analogues of the Quararibea metabolite chiral enolic-γ-lactone from (2S,3S)- and (2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acids
  作者：Chithra Gopinath、Salini Thomas、Mangalam S. Nair、Ibrahim Ibnusaud

  DOI：10.1016/j.tetlet.2006.08.133

  日期：2006.11

  Reaction of dialkyl (2S,3S)- or (2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylates with POCl3 in pyridine followed by diazomethane resulted in the isolation of dialkyl 2S-4-methoxy-5-oxo-2,5-dihydro-2,3-furandicarboxylates, which are analogues of the Quararibea metabolite chiral enolic-gamma-lactone (3-hydroxy-4,5-(R)-dimethyl-2(5H)-furanone). An unusual alpha-hydroxylation of gamma-butyrolactone takes place involving POCl3 in pyridine. When the dehydration was facilitated with methanesulfonyl chloride in triethylamine, instead of POCl3, aromatic dialkyl 5-[(methylsulfonyl)oxy]-2,3-furandicarboxylates were obtained. (c) 2006 Elsevier Ltd. All rights reserved.