(3S,7R,11R,15R)-1,11,16-trihydroxy-3,7,11,15-tetramethylhexadecan-4-one | 1350643-03-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,7R,11R,15R)-1,11,16-trihydroxy-3,7,11,15-tetramethylhexadecan-4-one
• CAS: 1350643-03-6
• 化学式: C₂₀H₄₀O₄
• 分子量: 344.535
• InChiKey: KVWYIWRSDKQRFM-FTEYMNFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,7R,11R,15R)-1,11,16-trihydroxy-3,7,11,15-tetramethylhexadecan-4-one 、 (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis and Spectroscopic Analysis of a Stereoisomer Library of the Phytophthora Mating Hormone α1 and Derived Bis-Mosher Esters

  摘要：

  Fluorous mixture synthesis provided all eight diastereomers of the phytophthora hormone alpha 1 with the R configuration at C11 as individual samples after demixing and detagging. The library of all possible bis-Mosher esters (16) was then made by esterification. Complete sets of H-1, C-13, and (for the Mosher esters) F-19 NMR spectra were recorded, assigned, and compared with each other and with published spectra. Not all of the spectra are unique, and the H-1 NMR spectra of the Mosher esters provided the most information. The previous assignment of the natural sample as an "all-R" stereoisomer mixed with its 3S-epimer was confirmed.

  DOI：

  10.1021/ja2082679
• 作为产物：
  描述：

  (3S,7R,11R,15R)-1-(4-(4,4,4-trifluorobutoxy)benzyloxy)-16-(4-(4,4,5,5,6,6,7,7,7-nonafluoroheptyloxy)benzyloxy)-11-hydroxy-3,7,11,15-tetramethylhexadecan-4-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 以64%的产率得到(3S,7R,11R,15R)-1,11,16-trihydroxy-3,7,11,15-tetramethylhexadecan-4-one
  参考文献：
  名称：

  Synthesis and Spectroscopic Analysis of a Stereoisomer Library of the Phytophthora Mating Hormone α1 and Derived Bis-Mosher Esters

  摘要：

  Fluorous mixture synthesis provided all eight diastereomers of the phytophthora hormone alpha 1 with the R configuration at C11 as individual samples after demixing and detagging. The library of all possible bis-Mosher esters (16) was then made by esterification. Complete sets of H-1, C-13, and (for the Mosher esters) F-19 NMR spectra were recorded, assigned, and compared with each other and with published spectra. Not all of the spectra are unique, and the H-1 NMR spectra of the Mosher esters provided the most information. The previous assignment of the natural sample as an "all-R" stereoisomer mixed with its 3S-epimer was confirmed.

  DOI：

  10.1021/ja2082679

文献信息

• Short Stereoselective Synthesis of the<i>Phytophthora</i>Universal Mating Hormone α1 Using Lithiation/Borylation Reactions
  作者：Alexander P. Pulis、Philipp Fackler、Varinder K. Aggarwal

  DOI：10.1002/anie.201400714

  日期：2014.4.22

  The universal mating hormone α 1 of the virulent plant pathogen Phytophthora has been synthesized in 12 steps and 28 % overall yield. Key CC bond‐forming steps involved the use of two lithiation/borylation reactions to couple together enantioenriched building blocks, one of which also set up the stereochemistry of the tertiary alcohol at C11. Detailed analysis showed that the diastereomeric purity

  毒性植物病原菌疫霉的通用交配激素α1已通过12个步骤合成，总产率为28％。密钥C  C键形成步骤涉及使用两个锂化/硼基化反应来耦合在一起对映体富集积木，其中之一也设置在C11叔醇的立体化学。详细分析表明，目标分子的非对映异构体纯度> 91％，是迄今为止获得的最高纯度。