6α-hydroxy-5α-cholestan-3β-yl acetate | 1256-82-2

• 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: 6α-hydroxy-5α-cholestan-3β-yl acetate
• 英文别名: 3β-acetoxy-5α-cholestan-6α-ol
• CAS: 1256-82-2
• 化学式: C₂₉H₅₀O₃
• 分子量: 446.714
• InChiKey: CKNKAHPLLXYVGQ-NRDPMAAJSA-N

物化性质

• 熔点：
  127-128 °C
• 沸点：
  516.1±33.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6α-hydroxy-5α-cholestan-3β-yl acetate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 3beta-乙酰氧基-5alpha-胆甾烷-6-酮
  参考文献：
  名称：

  Orientation of Fluorinated Cholesterol in Lipid Bilayers Analyzed by ¹⁹F Tensor Calculation and Solid-State NMR

  摘要：

  6-F-cholesterol was reported to exhibit biological and interfacial properties similar to unmodified cholesterol. We have also found that 6-F-cholesterol mimicked the cholesterol activity observed in the systems of amphotericin B and lipid rafts. However, to use 6-F-cholesterol as a molecular probe to explore molecular recognition in membranes, it is indispensable to have detailed knowledge of the dynamic and orientation properties of the molecule in membrane environments. In this paper, we present the molecular orientation of 6-F-cholesterol (30 mol %) in dimyristoylphosphatidylcholine (DMPC) bilayers revealed by combined use of F-19 chemical shift anisotropy (CSA), H-2 NMR, and C-F rotational echo double resonance (REDOR) experiments. The axis of rotation of 6-F-cholesterol was shown to be in a similar direction to that of cholesterol in DMPC bilayers, which is almost parallel to the long axis of the molecular frame. The molecular order parameter of 6-F-cholesterol was determined to be ca. 0.85, which is within the range of reported values of cholesterol. These findings suggest that the dynamic properties of 6-F-cholesterol in DMPC are quite similar to those of unmodified cholesterol; therefore, the introduction of a fluorine atom at C6 has virtually no effect on cholesterol dynamics in membranes. In addition, this study demonstrates the practical utility of theoretical calculations for determining the F-19 CSA principal axes, which would be extremely difficult to obtain experimentally. The combined use of quantum calculations and solid-state F-19 NMR will make it possible to apply the orientation information of F-19 CSA tensors to membrane systems.

  DOI：

  10.1021/ja077580l
• 作为产物：
  描述：

  3β-acetoxy-6β-bromo-5α-butanoyloxycholestane 在 三氟化硼四氢呋喃络合物 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.33h， 生成 6α-hydroxy-5α-cholestan-3β-yl acetate
  参考文献：
  名称：

  Beckwith, Athelstan L. J.; Duggan, Peter J., Journal of the Chemical Society. Perkin transactions II, 1992, # 10, p. 1777 - 1783

  摘要：

  DOI：

文献信息

• Hemisynthesis of (20S,24R)-20,24-epoxy-3β,16β,25-trihydroxy-6-oxo-5α-cholestane 16-acetate from diosgenin
  作者：Regina Tavares、Thierry Randoux、Jean-Claude Braekman、Désiré Daloze

  DOI：10.1016/s0040-4020(01)81873-1

  日期：1993.6.4

  The title compound which was isolated as its 3beta-sophoroside from the defensive secretion of Chrysomela varians (Coleoptera: Chrysomelidae) has been synthesized from diosgenin ih 8 steps.
• Synthesis of the sulfates derived from 5α-cholestane-3β, 6α-diol
  作者：Libuše M. Arnoštová、Vladimír Pouzar、Pavel Drašar

  DOI：10.1016/0039-128x(92)90107-k

  日期：1992.5

  Three new steroid sulfates-3-beta-hydroxy-5-alpha-cholestan-6-alpha-yl sulfate, 6-alpha-hydroxy-5-alpha-cholestan-3-beta-yl sulfate, and 5-alpha-cholestan-3-beta,6-alpha-diyl disulfate-were synthesized. For the syntheses of the key intermediates, 3-beta-hydroxy-5-alpha-cholestan-6-alpha-yl acetate and 6-alpha-hydroxy-5-alpha-cholestan-3-beta-yl acetate, selective protection of hydroxy groups in 5-alpha-cholestane-3-beta,6-alpha-diol was necessary. This problem was solved by using a combination of acetyl, tetrahydropyranyl, and methoxymethyl protective groups, which represents a new approach leading to these hydroxy acetates. Sulfated derivatives of 5-alpha-cholestane-3-beta,6-alpha-diol are present in marine invertebrates and were synthesized for the purposes of biologic testing.