(S)-1-((2S,5R)-5-((R)-1-hydroxypentadecyl)tetrahydrofuran-2-yl)tridec-12-en-1-ol | 1186603-81-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-1-((2S,5R)-5-((R)-1-hydroxypentadecyl)tetrahydrofuran-2-yl)tridec-12-en-1-ol
• 英文别名: (1R)-1-[(2R,5S)-5-[(1S)-1-hydroxytridec-12-enyl]oxolan-2-yl]pentadecan-1-ol
• CAS: 1186603-81-5
• 化学式: C₃₂H₆₂O₃
• 分子量: 494.842
• InChiKey: KWEBLDHLBMHKAE-MLMSKLGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  35
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(p-nitrobenzyl) 4-hydroxy-2-pentynoate 、 (S)-1-((2S,5R)-5-((R)-1-hydroxypentadecyl)tetrahydrofuran-2-yl)tridec-12-en-1-ol 在 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以70%的产率得到(4E)-4,5-didehydro-cis-uvariamicin I
  参考文献：
  名称：

  Total Synthesis and Stereochemical Assignment of cis-Uvariamicin I and cis-Reticulatacin

  摘要：

  Diastereoisomeric mixtures of cis-uvariamicin I (15R,16R,19S,20S,36S and 15S,16S,19R,20R,36S) and cis-reticulatacin (17R, 18R,21S,22S,36S and 17S,18S,21R,22 R,36S) were synthesized to determine the stereochemistry of the natural products isolated from Annona muricata. It was not possible to resolve I mixture of the four synthetic isomers using chiral HPLC, but the mixed isomers could be distinguished using chiral HPLC EIMS with extracted fragment ion analysis. Comparison of synthetic standards with the natural isolate revealed that cis-uvariamicin I and cis-reticulatacin are present in nature as Mixtures of threo-cis-threo diastereoisomers. It is suggested that the nomenclature for the natural products is amended as follows: (15R,16R,19S,20S,36S)-cis-uvariamicin I (cis-uvaramicin IA); (15S,16S,19R,20R,36S)-cis-uvariamicin I (cis-uvariamicin IB); (17R,18R,21S,22S,36S)-cis-reticulatacin (cis-reticulatacin A); (17S,18S,21R,22R,36S)-cis-reticulatacin (cis-reticulatacin B).

  DOI：

  10.1021/jo9012578
• 作为产物：
  描述：

  (R)-1-((2R,5S)-5-((S)-oxiran-2-yl)tetrahydrofuran-2-yl)pentadecan-1-ol 、 magnesium,undec-1-ene,bromide 在 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到(S)-1-((2S,5R)-5-((R)-1-hydroxypentadecyl)tetrahydrofuran-2-yl)tridec-12-en-1-ol
  参考文献：
  名称：

  Total Synthesis and Stereochemical Assignment of cis-Uvariamicin I and cis-Reticulatacin

  摘要：

  Diastereoisomeric mixtures of cis-uvariamicin I (15R,16R,19S,20S,36S and 15S,16S,19R,20R,36S) and cis-reticulatacin (17R, 18R,21S,22S,36S and 17S,18S,21R,22 R,36S) were synthesized to determine the stereochemistry of the natural products isolated from Annona muricata. It was not possible to resolve I mixture of the four synthetic isomers using chiral HPLC, but the mixed isomers could be distinguished using chiral HPLC EIMS with extracted fragment ion analysis. Comparison of synthetic standards with the natural isolate revealed that cis-uvariamicin I and cis-reticulatacin are present in nature as Mixtures of threo-cis-threo diastereoisomers. It is suggested that the nomenclature for the natural products is amended as follows: (15R,16R,19S,20S,36S)-cis-uvariamicin I (cis-uvaramicin IA); (15S,16S,19R,20R,36S)-cis-uvariamicin I (cis-uvariamicin IB); (17R,18R,21S,22S,36S)-cis-reticulatacin (cis-reticulatacin A); (17S,18S,21R,22R,36S)-cis-reticulatacin (cis-reticulatacin B).

  DOI：

  10.1021/jo9012578

文献信息

• Total Synthesis and Stereochemical Assignment of <i>cis</i>-Uvariamicin I and <i>cis</i>-Reticulatacin
  作者：Sherif B. Abdel Ghani、James M. Chapman、Bruno Figadère、Julie M. Herniman、G. John Langley、Scott Niemann、Richard C. D. Brown

  DOI：10.1021/jo9012578

  日期：2009.9.18

  Diastereoisomeric mixtures of cis-uvariamicin I (15R,16R,19S,20S,36S and 15S,16S,19R,20R,36S) and cis-reticulatacin (17R, 18R,21S,22S,36S and 17S,18S,21R,22 R,36S) were synthesized to determine the stereochemistry of the natural products isolated from Annona muricata. It was not possible to resolve I mixture of the four synthetic isomers using chiral HPLC, but the mixed isomers could be distinguished using chiral HPLC EIMS with extracted fragment ion analysis. Comparison of synthetic standards with the natural isolate revealed that cis-uvariamicin I and cis-reticulatacin are present in nature as Mixtures of threo-cis-threo diastereoisomers. It is suggested that the nomenclature for the natural products is amended as follows: (15R,16R,19S,20S,36S)-cis-uvariamicin I (cis-uvaramicin IA); (15S,16S,19R,20R,36S)-cis-uvariamicin I (cis-uvariamicin IB); (17R,18R,21S,22S,36S)-cis-reticulatacin (cis-reticulatacin A); (17S,18S,21R,22R,36S)-cis-reticulatacin (cis-reticulatacin B).