4α,5-epoxy-5α-cholestane-3α,6β-diol | 362594-61-4

• 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: 4α,5-epoxy-5α-cholestane-3α,6β-diol
• 英文别名: 4α,5α-epoxycholestane-3α,6β-diol；4α,5-epoxy-5α-cholestane-3β,6β-diol；(1S,2R,5R,6R,8R,9R,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadecane-5,9-diol
• CAS: 362594-61-4
• 化学式: C₂₇H₄₆O₃
• 分子量: 418.66
• InChiKey: DSORQMSYEPNHTP-DCRNWNMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4α,5-epoxy-5α-cholestane-3α,6β-diol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以79%的产率得到cholestane-3α,5α,6β-triol
  参考文献：
  名称：

  4,5-Epoxycholestane-3,6-diols: Templates for generating the full set of eight cholestane-3,5,6-triol stereoisomers in multigram scales, but not for a cholestane-3,4,6-triol

  摘要：

  Cholestane-3 beta,5 alpha,6 beta-triol is an extensively studied biologically important oxysterol. The full set of eight cholestane-3,5,6-triol stereoisomers was synthesised in diastereomerically pure forms by the stereoselective cleavage of eight diastereomerically pure 4,5-epoxycholestane-3,6-diols with LiAlH4, in high yields on multigram scales and without chromatography for most of them. However, applying various reportedly successful combinations of a hydride donor and a Lewis acid to the same substrates under a variety of conditions failed to generate a single unsubstituted cholestane-3,4,6-triol. The products of the eight cholestane-3,5,6-triol stereoisomers will serve as a good probe in the study of biological functions of oxysterols in a biological process. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.11.015
• 作为产物：
  描述：

  Acetic acid (3R,4R,5R,6R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-3-hydroxy-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[4,5]cyclopenta[a]phenanthren-6-yl ester 在 sodium hydroxide 作用下， 生成 4α,5-epoxy-5α-cholestane-3α,6β-diol
  参考文献：
  名称：

  甾体骨架中双脂环族醇的立体控制环氧化的研究：从cholest-4-en-3β，6β-制备八种非对映体纯的环氧化物；-3β，6α-; -3α，6β-和-3α，6α-二醇

  摘要：

  从cholest-4-en-3β，6β制备了八种非对映体纯的环氧化物；-3β，6α-; -3α，6β-和-3α，6α-二醇通过空间，保护基和氧化剂的组合作用对甾体骨架内双脂环式醇系统的立体控制的环氧化作用。

  DOI：

  10.1016/s0957-4166(01)00174-4

文献信息

• Reactivity of Steroidal Dienes towards the Methyltrioxorhenium/H2O2−Urea Oxidation System: Isolation and Characterization of New Oxygenated Steroids
  作者：Donato Sica、Domenica Musumeci、Franco Zollo、Simona De Marino

  DOI：10.1002/1099-0690(200110)2001:19<3731::aid-ejoc3731>3.0.co;2-2

  日期：2001.10

  solvents, and in the presence of pyridine as ligand. Three new 4,5-epoxy-3,6-dihydroxyl compounds 10, 11, and 12 were isolated from the treatment of diene 4 in CHCl3 at 0 °C, while oxidations of the Δ7,9(11)-diene steroid 13 allowed us to isolate the new monoepoxy and diepoxy steroids 14 and 15 and the new triol 19. The structures of all new steroids were verified on the basis of chemical evidence and interpretation

  为了检查共轭二烯类固醇对甲基三氧铼 (MTO) 催化氧化与尿素-过氧化氢加合物 (UHP) 的反应性及其在类固醇核环官能化中的可能用途，MTO/UHP 系统与胆甾醇的反应研究了非质子溶剂中的 -3,5-二烯 (4) 和 5α-胆甾醇-7,9(11)-二烯-3β-基乙酸酯 (13)。这些氧化在 0 °C 和 25 °C 下进行，在 CHCl3 或乙醚作为溶剂中，并在吡啶作为配体的存在下进行。在 0 °C 的 CHCl3 中处理二烯 4 时分离出了三种新的 4,5-环氧-3,6-二羟基化合物 10、11 和 12，同时允许 Δ7,9(11)-二烯类固醇 13 氧化我们分离出新的单环氧和双环氧类固醇 14 和 15 以及新的三醇 19。
• Studies on stereocontrolled epoxidations of bis-alicyclic alcohols in steroidal skeletons: preparation of eight diastereomerically pure epoxides from cholest-4-en-3β,6β-; -3β,6α-; -3α,6β- and -3α,6α-diols
  作者：Kejun Zhao、Yongfeng Wang、David C. Billington

  DOI：10.1016/s0957-4166(01)00174-4

  日期：2001.5

  Eight diastereomerically pure epoxides have been prepared from cholest-4-en-3β,6β; -3β,6α-; -3α,6β- and -3α,6α-diols via a combination of steric, protecting group and oxidant effects on stereocontrolled epoxidations of a bis-alicyclic alcohol system within the steroidal skeleton.

  从cholest-4-en-3β，6β制备了八种非对映体纯的环氧化物；-3β，6α-; -3α，6β-和-3α，6α-二醇通过空间，保护基和氧化剂的组合作用对甾体骨架内双脂环式醇系统的立体控制的环氧化作用。
• 4,5-Epoxycholestane-3,6-diols: Templates for generating the full set of eight cholestane-3,5,6-triol stereoisomers in multigram scales, but not for a cholestane-3,4,6-triol
  作者：Kejun Zhao、Yongfeng Wang、Li Han

  DOI：10.1016/j.steroids.2006.11.015

  日期：2007.1

  Cholestane-3 beta,5 alpha,6 beta-triol is an extensively studied biologically important oxysterol. The full set of eight cholestane-3,5,6-triol stereoisomers was synthesised in diastereomerically pure forms by the stereoselective cleavage of eight diastereomerically pure 4,5-epoxycholestane-3,6-diols with LiAlH4, in high yields on multigram scales and without chromatography for most of them. However, applying various reportedly successful combinations of a hydride donor and a Lewis acid to the same substrates under a variety of conditions failed to generate a single unsubstituted cholestane-3,4,6-triol. The products of the eight cholestane-3,5,6-triol stereoisomers will serve as a good probe in the study of biological functions of oxysterols in a biological process. (c) 2006 Elsevier Inc. All rights reserved.