[(2S,3R,4R,5S,6R)-4,5-diacetyloxy-2-methyl-6-octadec-9-enylsulfanyloxan-3-yl] acetate | 75014-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4R,5S,6R)-4,5-diacetyloxy-2-methyl-6-octadec-9-enylsulfanyloxan-3-yl] acetate
• CAS: 75014-53-8
• 化学式: C₃₀H₅₂O₇S
• 分子量: 556.805
• InChiKey: XXUFLUMWHJOKRD-VGYFXUJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  38.0
• 可旋转键数：
  20.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4R,5S,6R)-4,5-diacetyloxy-2-methyl-6-octadec-9-enylsulfanyloxan-3-yl] acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以67%的产率得到oleyl 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
• 作为产物：
  描述：

  oleyl iodide 、 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranose 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以61%的产率得到[(2S,3R,4R,5S,6R)-4,5-diacetyloxy-2-methyl-6-octadec-9-enylsulfanyloxan-3-yl] acetate
  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