hexadecyl 1-thio-β-L-fucopyranoside | 75014-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hexadecyl 1-thio-β-L-fucopyranoside
• 英文别名: (2R,3S,4R,5S,6S)-2-hexadecylsulfanyl-6-methyloxane-3,4,5-triol
• CAS: 75014-37-8
• 化学式: C₂₂H₄₄O₄S
• 分子量: 404.655
• InChiKey: XNLULLOLEFYNIV-AHJNKEMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  95.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranose 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 hexadecyl 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

文献信息

• New glycolipid compounds, process for preparation and use as immunological adjuvant
  申请人：Merck & Co., Inc.

  公开号：EP0023865A2

  公开（公告）日：1981-02-11

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

  Y-R 式中 Y 为 1-硫代-B-L-岩藻糖、1-硫代-B-D-半乳糖或 1-硫代-B-乳糖，R 为 2-(1-金刚烷基)乙基、3-[(对氟苯乙基)苯基]丙基、6-(5-胆甾烯-3B-氧基)己-3-炔基、油基或十六烷基的化合物是疫苗中有用的免疫佐剂。
• US4259324A
  申请人：——

  公开号：US4259324A

  公开（公告）日：1981-03-31
• Glycolipids as potential immunologic adjuvants
  作者：Mitree M. Ponpipom、Robert L. Bugianesi、Tsung-Ying Shen

  DOI：10.1021/jm00185a007

  日期：1980.11

  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.