Testosterone 2,3,4,6-tetra-O-benzoyl-β-L-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: Testosterone 2,3,4,6-tetra-O-benzoyl-β-L-glucopyranoside
• 英文别名: [(2S,3S,4R,5S,6S)-3,4,5-tribenzoyloxy-6-[[(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]oxy]oxan-2-yl]methyl benzoate
• 化学式: C₅₃H₅₄O₁₁
• 分子量: 867.005
• InChiKey: IOHNGWAQGNSQBC-VDUBXKEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  64
• 可旋转键数：
  15
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1,2,3,4,6-Penta-O-benzoyl-L-glucopyranoside 在 氢溴酸 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 0.5h， 生成 Testosterone 2,3,4,6-tetra-O-benzoyl-β-L-glucopyranoside
  参考文献：
  名称：

  Tetra-O-benzoylglucosylation: A New 1H Nuclear Magnetic Resonance Method for Determination of the Absolute Configuration of Secondary Alcohols

  摘要：

  A new method for determination of the absolute configuration of secondary alcohols based on the anisotropic effect and glycosylation-induced H-1 NMR shifts is described. The tetra-O-benzoyl-beta-glucosylation of secondary alcohols induces dramatic shifts in the aglycon H-1 NMR peaks. The differences between the proton chemical shifts of the D-glucosylated derivative and the free alcohol (Delta delta = delta(D) - delta(ROH)) or more significantly between their chemical shifts in the D- and L-glucosylated derivatives (Delta delta = delta(D) - delta(L)) are characteristic of the absolute configuration of the secondary chiral alcohol. Furthermore, in most cases the sign of the chemical shift difference of the carbinyl protons correlates with the absolute configuration of their carbons, namely positive or negative Delta delta are obtained for (R)- or (S)-carbinyl carbons, respectively. Moreover, this method involves the use of one enantiomer and generally a single derivatization is sufficient.

  DOI：

  10.1021/jo00101a023

文献信息

• Tetra-O-benzoylglucosylation: A New 1H Nuclear Magnetic Resonance Method for Determination of the Absolute Configuration of Secondary Alcohols
  作者：Mar Trujillo、Ezequiel Q. Morales、Jesus T. Vazquez

  DOI：10.1021/jo00101a023

  日期：1994.11

  A new method for determination of the absolute configuration of secondary alcohols based on the anisotropic effect and glycosylation-induced H-1 NMR shifts is described. The tetra-O-benzoyl-beta-glucosylation of secondary alcohols induces dramatic shifts in the aglycon H-1 NMR peaks. The differences between the proton chemical shifts of the D-glucosylated derivative and the free alcohol (Delta delta = delta(D) - delta(ROH)) or more significantly between their chemical shifts in the D- and L-glucosylated derivatives (Delta delta = delta(D) - delta(L)) are characteristic of the absolute configuration of the secondary chiral alcohol. Furthermore, in most cases the sign of the chemical shift difference of the carbinyl protons correlates with the absolute configuration of their carbons, namely positive or negative Delta delta are obtained for (R)- or (S)-carbinyl carbons, respectively. Moreover, this method involves the use of one enantiomer and generally a single derivatization is sufficient.