(24R)-24-ethyl-5-cholesten-3β-yl formate

• 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: (24R)-24-ethyl-5-cholesten-3β-yl formate
• 英文别名: stigmast-5-ene-3β-yl formate；β-sitosterol formate；3β-sitosteryl formate；[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] formate
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: OLLAJSNLQPFYSL-VHZNKUSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  植物甾醇 在 吡啶 、 水 、 sodium acetate 作用下， 反应 22.0h， 生成 (24R)-24-ethyl-5-cholesten-3β-yl formate
  参考文献：
  名称：

  Solvolysis of sterol tosylates in aqueous dimethylformamide

  摘要：

  In has been established that the heating of the sterol tosylates (Ia--c) in aqueous dimethylformamide in the presence of sodium acetate leads to the formation of the 3a,5-cyclo-6 beta-alcohols (2), the sterols (3), the 3,5-dienes (4), and the sterol formates (5).

  DOI：

  10.1007/bf02234855

文献信息

• A simple, convenient and chemoselective formylation of sterols by Vilsmeier reagent
  作者：Vandana Srivastava、Arvind Singh Negi、J.K. Kumar、M.M. Gupta

  DOI：10.1016/j.steroids.2006.03.005

  日期：2006.7

  Vilsmeier reagent (DMF-POCl3) was used as an efficient formylating agent. Several sterols having sec-hydroxyl group at 3/17-position have been modified into respective formate esters. The method is simple, mild, chemoselective and provides sec-alcoholic protection in good yields. (c) 2006 Elsevier Inc. All rights reserved.
• Solvolysis of sterol tosylates in aqueous dimethylformamide
  作者：N. V. Kovganko、V. L. Survilo

  DOI：10.1007/bf02234855

  日期：1999.5

  In has been established that the heating of the sterol tosylates (Ia--c) in aqueous dimethylformamide in the presence of sodium acetate leads to the formation of the 3a,5-cyclo-6 beta-alcohols (2), the sterols (3), the 3,5-dienes (4), and the sterol formates (5).