6-(5-cholesten-3β-yloxy)-3-hexynyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside | 75014-58-3

• 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-hexynyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside
• CAS: 75014-58-3
• 化学式: C₄₅H₇₀O₈S
• 分子量: 771.112
• InChiKey: BALKTRNRDHXFTQ-RUWPLRGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.47
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  6-(5-cholesten-3β-yloxy)-3-hexynyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以65%的产率得到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 吡啶 、 溶剂黄146 、 苯基锂 、 三乙胺 、 sodium iodide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 丁酮 为溶剂， 反应 60.0h， 生成 6-(5-cholesten-3β-yloxy)-3-hexynyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside
  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