2,2-dihexadecyl-1,3-bis[(β-D-galactopyranosyl)oxy]propane | 197638-47-4

• 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: 2,2-dihexadecyl-1,3-bis[(β-D-galactopyranosyl)oxy]propane
• 英文别名: (2R,3R,4S,5R,6R)-2-[2-hexadecyl-2-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]octadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 197638-47-4
• 化学式: C₄₇H₉₂O₁₂
• 分子量: 849.24
• InChiKey: DAKSEYGQJGGVLR-HCDZPIIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  59
• 可旋转键数：
  38
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  199
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,2-dihexadecyl-1,3-bis[(β-D-galactopyranosyl)oxy]propane 在 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 32.5h， 生成
  参考文献：
  名称：

  Synthetic Studies on Selectin Ligands/Inhibitors: Synthesis and Biological Activity of the Sulfated and Phosphorylated Multivalent β-D-Galactopyranosides Containing Fatty Alkyl Residues

  摘要：

  Ten sulfated and three phosphorylated beta-D-galactopyranoside dimers and one sulfated beta-D-galactopyranoside trimer containing fatty alkyl residues in place of ceramide have been synthesized. The coupling of 2,3,4,6-tetra-0-acetyl-alpha-D-galactopyranosyl bromide (2) with branched fatty alkyl diols and a triol (1a-1j) using mercury bromide as an activating agent gave the corresponding parent glycolipids (4a-4j) in good yields. Regioselective sulfation of these parent glycolipids through the dibutylstannylene acetals produced the target sulfated glycolipids, 3-sulfate (5a-5j) while stepwise phosphorylation with dibenzyloxy(diisopropylamino)phosphine gave the phosphorylated glycolipids, 3,4-bisphosphate (9e, g, i). The synthetic glycolipids were assayed for their ability to block the adhesion of HL-60 cells to immobilized P-, L- and E-selectin.

  DOI：

  10.1080/07328309808002333
• 作为产物：
  描述：

  [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-hexadecyl-2-[[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxymethyl]octadecoxy]oxan-2-yl]methyl acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以93%的产率得到2,2-dihexadecyl-1,3-bis[(β-D-galactopyranosyl)oxy]propane
  参考文献：
  名称：

  Synthetic Studies on Selectin Ligands/Inhibitors: Synthesis and Biological Activity of the Sulfated and Phosphorylated Multivalent β-D-Galactopyranosides Containing Fatty Alkyl Residues

  摘要：

  Ten sulfated and three phosphorylated beta-D-galactopyranoside dimers and one sulfated beta-D-galactopyranoside trimer containing fatty alkyl residues in place of ceramide have been synthesized. The coupling of 2,3,4,6-tetra-0-acetyl-alpha-D-galactopyranosyl bromide (2) with branched fatty alkyl diols and a triol (1a-1j) using mercury bromide as an activating agent gave the corresponding parent glycolipids (4a-4j) in good yields. Regioselective sulfation of these parent glycolipids through the dibutylstannylene acetals produced the target sulfated glycolipids, 3-sulfate (5a-5j) while stepwise phosphorylation with dibenzyloxy(diisopropylamino)phosphine gave the phosphorylated glycolipids, 3,4-bisphosphate (9e, g, i). The synthetic glycolipids were assayed for their ability to block the adhesion of HL-60 cells to immobilized P-, L- and E-selectin.

  DOI：

  10.1080/07328309808002333