Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-dodecyloxy]-tetrahydro-pyran-4-yl ester | 212761-01-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-dodecyloxy]-tetrahydro-pyran-4-yl ester
• CAS: 212761-01-8
• 化学式: C₄₁H₆₄O₂₀
• 分子量: 876.947
• InChiKey: ABASYDTUAVCXCA-UFGBQNHSSA-N

物化性质

• 沸点：
  786.184±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.236±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  61.0
• 可旋转键数：
  25.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  247.32
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-dodecyloxy]-tetrahydro-pyran-4-yl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以99%的产率得到2-decyl-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
• 作为产物：
  描述：

  2-癸基丙烷-1,3-二醇 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 copper(II) sulfate 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 1,2-二氯乙烷 为溶剂， 以63%的产率得到Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-dodecyloxy]-tetrahydro-pyran-4-yl ester
  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