6-(5-cholesten-3β-yloxy)-3-hexyn-1-ol | 75014-49-2

• 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: 6-(5-cholesten-3β-yloxy)-3-hexyn-1-ol
• 英文别名: 6-(5-Cholesten-3beta-yloxy)hex-3-yne-1-ol；6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]hex-3-yn-1-ol
• CAS: 75014-49-2
• 化学式: C₃₃H₅₄O₂
• 分子量: 482.791
• InChiKey: AZYYKCWTFLZTRN-IJXDZZBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(5-cholesten-3β-yloxy)-3-hexyn-1-ol 在 吡啶 、 sodium methylate 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 丁酮 为溶剂， 反应 52.0h， 生成 2-((6-((10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)hex-3-yn-1-yl)thio)-6-methyltetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Glycolipids as potential immunologic adjuvants

  摘要：

  A group of 1-thio-beta-L-fucopyranosides containing hexadecane, 9-octadecene, adamantane, 1,2-diphenyltetrafluoroethane, and 3-hexynyl- and 3,6-dioxaoctylcholesterols were synthesized as potential immunologic adjuvants. Many of these fucosyl lipids and 6-(5-cholesten-3 beta-yloxy)hexyl 1 thioglycosides were found to give good response to subunit A/Victoria influenza virus. Carbohydrates with L-fucose and D-galactose backbones appeared essential for adjuvant activity. Lactose which has a terminal D-galactose moiety was found to be active, whereas L-arabinose which lacks a 5-(hydroxymethyl) group was inactive.

  DOI：

  10.1021/jm00185a007
• 作为产物：
  描述：

  2-(5-cholesten-3β-yloxy)ethyl iodide 在 苯基锂 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 6-(5-cholesten-3β-yloxy)-3-hexyn-1-ol
  参考文献：
  名称：

  Glycolipids as potential immunologic adjuvants

  摘要：

  A group of 1-thio-beta-L-fucopyranosides containing hexadecane, 9-octadecene, adamantane, 1,2-diphenyltetrafluoroethane, and 3-hexynyl- and 3,6-dioxaoctylcholesterols were synthesized as potential immunologic adjuvants. Many of these fucosyl lipids and 6-(5-cholesten-3 beta-yloxy)hexyl 1 thioglycosides were found to give good response to subunit A/Victoria influenza virus. Carbohydrates with L-fucose and D-galactose backbones appeared essential for adjuvant activity. Lactose which has a terminal D-galactose moiety was found to be active, whereas L-arabinose which lacks a 5-(hydroxymethyl) group was inactive.

  DOI：

  10.1021/jm00185a007

文献信息

• Immunologic adjuvant thio glycoside compounds and compositions
  申请人：Merck & Co., Inc.

  公开号：US04259324A1

  公开（公告）日：1981-03-31

  Compounds of the formulae Y--R wherein Y is 1-thio-.beta.-L-fucose, 1-thio-.beta.-D-galactose or 1-thio-.beta.-lactose and R is 2-(1-adamantyl)ethyl, 3-[(p-tetrafluorophenethyl)phenyl]propyl, 6-(5-cholesten-3.beta.-yloxy)hex-3-ynl, oleyl, or hexadecyl are useful immunologic adjuvants in vaccines.

  公式为Y--R的化合物，其中Y是1-硫代-β-L-岩藻糖、1-硫代-β-D-半乳糖或1-硫代-β-乳糖，而R是2-(1-金刚烷基)乙基、3-[(对四氟苯乙基)苯基]丙基、6-(5-胆甾-3β-氧基)己-3-炔基、油酸或十六烷基，可用作疫苗中的免疫佐剂。