1-deoxy-1-(1H-pyrrol-1-yl)-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose | 1338805-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1-deoxy-1-(1H-pyrrol-1-yl)-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
• 英文别名: 1-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl]pyrrole
• CAS: 1338805-39-2
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: ZOPZPNLIFLGYHH-FOCJUVANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-(1H-pyrrol-1-yl)-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose 在 manganese(IV) oxide 、 水 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 15.0h， 生成 1-(((3aS,6R,7R,7aS)-6,7-dihydroxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-3a-yl)methyl)-1H-pyrrole-2,5-dicarbaldehyde
  参考文献：
  名称：

  Total Synthesis of Two Pyrrole Spiroketal Alkaloids: Pollenopyrroside A and Capparisine B

  摘要：

  Pollenopyrroside A and capparisine B, two diastereoisomers of pyrrole spiroketal alkaloids isolated from Brassica campestris pollen and Capparis spinosa, were synthesized by an improved microwave-assisted bishydroxymethylation of pyrrole and acid-catalyzed spirocyclization as key steps with total yields of 2.7 and 8.8%, respectively.

  DOI：

  10.1055/s-0034-1380172
• 作为产物：
  描述：

  果糖二丙酮 在 磺酰氯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 11.0h， 生成 1-deoxy-1-(1H-pyrrol-1-yl)-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
  参考文献：
  名称：

  Synthesis of Novel N-carbohydrate-derived Heterocyclic Compounds by Nucleophilic Substitution Reaction of Carbohydrate Imidazole-1-sulfonates

  摘要：

  The nucleophilic substitution reaction of carbohydrate imidazole-1-sulfonates with pyrrole and other nitrogen heterocyclic compounds is reported for the first time. Several novel N-carbohydrate-derived heterocyclic compounds have been prepared by this displacement reaction. The desired carbon-nitrogen bond formation proceeds under mild conditions to generate the coupling products in good yields with readily available and inexpensive reagents. This method is particularly suitable for carbohydrate imidazole-1-sulfonates of primary alcohols. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the free supplemental file.

  DOI：

  10.1080/07328303.2011.605193

文献信息

• Synthesis of Novel N-carbohydrate-derived Heterocyclic Compounds by Nucleophilic Substitution Reaction of Carbohydrate Imidazole-1-sulfonates
  作者：Shiyong Huo、Yueqing Li、Chaoyan Liang、Jihong Liu、Weijie Zhao

  DOI：10.1080/07328303.2011.605193

  日期：2011.2.1

  The nucleophilic substitution reaction of carbohydrate imidazole-1-sulfonates with pyrrole and other nitrogen heterocyclic compounds is reported for the first time. Several novel N-carbohydrate-derived heterocyclic compounds have been prepared by this displacement reaction. The desired carbon-nitrogen bond formation proceeds under mild conditions to generate the coupling products in good yields with readily available and inexpensive reagents. This method is particularly suitable for carbohydrate imidazole-1-sulfonates of primary alcohols. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the free supplemental file.
• Total Synthesis of Two Pyrrole Spiroketal Alkaloids: Pollenopyrroside A and Capparisine B
  作者：Weijie Zhao、Zhi Cao、Yueqing Li、Shisheng Wang、Xiuhan Guo、Liu Wang

  DOI：10.1055/s-0034-1380172

  日期：——

  Pollenopyrroside A and capparisine B, two diastereoisomers of pyrrole spiroketal alkaloids isolated from Brassica campestris pollen and Capparis spinosa, were synthesized by an improved microwave-assisted bishydroxymethylation of pyrrole and acid-catalyzed spirocyclization as key steps with total yields of 2.7 and 8.8%, respectively.