2,3-O-isopropylidene-5-deoxy-D-ribono-1,4-lactone | 72127-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-5-deoxy-D-ribono-1,4-lactone
• 英文别名: 5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone；5-deoxy-2,3-isopropylidene-D-ribonolactone；(3aR,6R,6aR)-2,2,6-trimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 72127-43-6
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: YUGRZMZGERGITJ-HSUXUTPPSA-N

物化性质

• 沸点：
  263.1±35.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-5-deoxy-D-ribono-1,4-lactone 在 二异丁基氢化铝 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.5h， 生成 5-deoxy-D-ribose
  参考文献：
  名称：

  N^δ-(5-Hydroxy-4,6-dimethylpyrimidine-2-yl)-l-ornithine, a Novel Methylglyoxal−Arginine Modification in Beer

  摘要：

  N-delta-(5-Hydroxy-4,6-dimethylpyrimidine-2-yl)-L-ornithine, or Argpyrimidine, was identified and quantified in beer by high-performance liquid chromatography (HPLC) and coupled gas chromatography-mass spectrometry (HRGC-MS). This novel fluorescent arginine Maillard modification represents the first amino acid modification reported in beer retaining the full backbone of the original amino acid. Two mechanisms of formation could be verified: the major pathway via methylglyoxal and the minor pathway via 5-deoxypentoses. Argpyrimidine concentrations, determined in 35 lager-type beer varieties, reached up to 27 nmol/L and could be positively correlated to beer color and wort content. Within this context, 5-deoxy-D-ribose was identified as a novel intermediate of the Maillard reaction of maltose by HRGC-MS and independent synthesis.

  DOI：

  10.1021/jf000493r
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 草酰氯 、 偶氮二异丁腈 、 三正丁基氢锡 、 N,N-二甲基甲酰胺 作用下， 生成 2,3-O-isopropylidene-5-deoxy-D-ribono-1,4-lactone
  参考文献：
  名称：

  Chemistry of F1,F0-ATPase inhibitors. Stereoselective total syntheses of (+)-citreoviral and (-)-citreoviridin

  摘要：

  DOI：

  10.1021/ja00210a026

文献信息

• Total Synthesis of Penicyclone A Using a Double Grignard Reaction
  作者：Gregor Talajić、Edi Topić、Jerko Meštrović、Nikola Cindro

  DOI：10.1021/acs.joc.2c02200

  日期：2022.12.2

  We describe the first total synthesis of penicyclone A, a novel deep-sea fungus-derived polyketide, and a reevaluation of its antimicrobial activity. The synthesis of this unique spirolactone was achieved in 10 steps starting from a known d-ribose derivative. The key steps include a double Grignard reaction for the diastereoselective construction of the chiral tertiary alcohol intermediate, tandem

  我们描述了 penicyclone A 的首次全合成，这是一种新型的深海真菌衍生聚酮化合物，并重新评估了其抗菌活性。这种独特的螺内酯的合成是从一种已知的d -核糖衍生物开始，分 10 步完成的。关键步骤包括用于手性叔醇中间体的非对映选择性构建的双格氏反应、串联氧化/环化和光氧化，然后是氧化重排以引入烯酮功能。
• A facile synthesis of optically pure valerolactone and β-hydroxy valerolactone from a common sugar-derived precursor
  作者：Christos Papageorgiou、Claude Benezra

  DOI：10.1016/s0040-4039(01)81755-x

  日期：1984.1
• Chemistry of F1,F0-ATPase inhibitors. Stereoselective total syntheses of (+)-citreoviral and (-)-citreoviridin
  作者：Hongsuk. Suh、Craig S. Wilcox

  DOI：10.1021/ja00210a026

  日期：1988.1
• Synthesis, Conformational Analysis and Biological Evalution of 2-(5-Deoxy-b-D-ribofuranosyl)pyridine-4-carboxamide
  作者：Pieter E. Joos、Alex De Groot、Eddy L. Esmans、Frank C. Alderweireldt、André De Bruyn、Jan Balzarini、Erik De Clercq

  DOI：10.3987/com-94-s1

  日期：——
• <i>N</i>^δ-(5-Hydroxy-4,6-dimethylpyrimidine-2-yl)-<scp>l</scp>-ornithine, a Novel Methylglyoxal−Arginine Modification in Beer
  作者：Marcus A. Glomb、Daniel Rösch、Ramanakoppa H. Nagaraj

  DOI：10.1021/jf000493r

  日期：2001.1.1

  N-delta-(5-Hydroxy-4,6-dimethylpyrimidine-2-yl)-L-ornithine, or Argpyrimidine, was identified and quantified in beer by high-performance liquid chromatography (HPLC) and coupled gas chromatography-mass spectrometry (HRGC-MS). This novel fluorescent arginine Maillard modification represents the first amino acid modification reported in beer retaining the full backbone of the original amino acid. Two mechanisms of formation could be verified: the major pathway via methylglyoxal and the minor pathway via 5-deoxypentoses. Argpyrimidine concentrations, determined in 35 lager-type beer varieties, reached up to 27 nmol/L and could be positively correlated to beer color and wort content. Within this context, 5-deoxy-D-ribose was identified as a novel intermediate of the Maillard reaction of maltose by HRGC-MS and independent synthesis.