2-(tetradecyl)hexadecyl O-(3-O-sulfo-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside sodium salt

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(tetradecyl)hexadecyl O-(3-O-sulfo-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside sodium salt
• 英文别名: sodium;[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(2-tetradecylhexadecoxy)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] sulfate
• 化学式: C₄₂H₈₁O₁₄S*Na
• 分子量: 865.153
• InChiKey: UUQVTMANWDCRKD-VMYBVFCJSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  58
• 可旋转键数：
  35
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  233
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 在 sodium hydroxide 、 molecular sieve 、 三甲基氨基磺酸 、 三氟化硼乙醚 、 二正丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 2-(tetradecyl)hexadecyl O-(3-O-sulfo-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside sodium salt
  参考文献：
  名称：

  Synthetic Studies on Selectin Ligands/Inhibitors: One-Pot Synthesis of the Mono- and Oligo-Sulfated 2-(Tetradecyl)Hexadecyl β-D-Galacto- and Lactopyranosides as the Sulfatide Mimetics

  摘要：

  Regioselective sulfation through the dibutylstannylene acetals was applied to the key step to prepare a number of sulfated saccharides which are active as the inhibitors of L-and P-selectin. The number and the positions of the sulfate groups were confirmed by NMR and MS analyses. Using this methodology, our target sulfated glycolipids (6-9, 12-14) were conveniently synthesized in one-pot from free 2-(tetradecyl)hexadecyl beta-D-galactopyranoside 5 and lactoside 11.

  DOI：

  10.1080/07328309708006544

文献信息

• Synthetic Studies on Selectin Ligands/Inhibitors: A Systematic Synthesis of Sulfatide and Its Higher Congeners Carrying 2-(Tetradecyl)Hexadecyl Group as a Ceramide Substitute
  作者：Eiji Tanahashi、Katsutoshi Murase、Mika Shibuya、Yumie Igarashi、Hideharu Ishida、Akira Hasegawa、Makoto Kiso

  DOI：10.1080/07328309708006543

  日期：1997.8.1

  A systematic synthesis of sulfatide (I) and novel sulfatide analogs (II-VI) carrying 2-(tetradecyl)hexadecyl group as a ceramide substitute is described. The 3-O-, 4-O- and 3,4-di-O-levulinoyl derivatives of galactopyranosyl trichloroacetimidates (1, 12, and 13) were coupled with (2S,3R,4E)-3-O-acetyl-2-octadecanamido-4-octadecene-1,3-diol or 2-(tetradecyl)hexadecan-1-ol. The resulting glycolipids

  描述了带有2-（十四烷基）十六烷基作为神经酰胺替代物的硫化物（I）和新型硫化物类似物（II-VI）的系统合成。3- ø - ，4- ö -和3,4-二- ö -levulinoyl吡喃半乳糖基trichloroacetimidates（的衍生物1，12，和13）进行了与（2小号，3 - [R，4 ë）-3- ø -乙酰基-2-十八碳酰胺基-4-十八碳烯-1,3-二醇或2-（十四烷基）十六烷-1-醇。将得到的糖脂（2,4，14，和15）分别通过选择性除去乙酰丙酰基，连续硫酸化和去O-酰化反应分别转化为3-硫酸盐（I，II），4-硫酸盐（III）和3,4-二硫酸盐（四）。6-硫酸酯（V），由2-（十四烷基）制备的十六烷基β-d吡喃半乳糖苷（21）经由所述6- ø -吨丁基二衍生物，而2-（十四烷基）3'-硫酸十六烷基β-由2-（三甲基甲硅烷基）乙基3' - O-苄基-β-D-乳糖苷（26）合成
• Synthetic Studies on Selectin Ligands/Inhibitors: One-Pot Synthesis of the Mono- and Oligo-Sulfated 2-(Tetradecyl)Hexadecyl β-D-Galacto- and Lactopyranosides as the Sulfatide Mimetics
  作者：Takao Ikami、Hitoshi Hamajima、Toshinao Usui、Takahiko Mitani、Hideharu Ishida、Makoto Kiso、Akira Hasegawa

  DOI：10.1080/07328309708006544

  日期：1997.8.1

  Regioselective sulfation through the dibutylstannylene acetals was applied to the key step to prepare a number of sulfated saccharides which are active as the inhibitors of L-and P-selectin. The number and the positions of the sulfate groups were confirmed by NMR and MS analyses. Using this methodology, our target sulfated glycolipids (6-9, 12-14) were conveniently synthesized in one-pot from free 2-(tetradecyl)hexadecyl beta-D-galactopyranoside 5 and lactoside 11.