Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[2-decyl-2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-octadecyloxy]-tetrahydro-pyran-3-yl ester | 212761-19-8

• 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: Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[2-decyl-2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-octadecyloxy]-tetrahydro-pyran-3-yl ester
• CAS: 212761-19-8
• 化学式: C₅₇H₉₆O₂₀
• 分子量: 1101.38
• InChiKey: OYBCEGIMFFWDBL-PHTLTCMDSA-N

物化性质

• 沸点：
  913.870±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.142±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[2-decyl-2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-octadecyloxy]-tetrahydro-pyran-3-yl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以89%的产率得到
  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-Decyl-2-hexadecyl-propane-1,3-diol 、 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， 生成 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[2-decyl-2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-octadecyloxy]-tetrahydro-pyran-3-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