Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(12-iodo-dodecyloxy)-tetrahydro-pyran-4-yl ester | 251547-38-3

• 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,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(12-iodo-dodecyloxy)-tetrahydro-pyran-4-yl ester
• CAS: 251547-38-3
• 化学式: C₂₆H₄₃IO₁₀
• 分子量: 642.526
• InChiKey: OULGTFZMCPUVCH-WSGIOKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  37.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(12-iodo-dodecyloxy)-tetrahydro-pyran-4-yl ester 在 18-冠醚-6 、 4-Angstroem MS 、 potassium carbonate 、 三乙胺 、 potassium bromide 作用下， 以 二氯甲烷 、 乙腈 、 丁酮 为溶剂， 反应 9.0h， 生成 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(12-{3-bromomethyl-5-[12-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-dodecyloxy]-phenoxy}-dodecyloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of targetable cationic amphiphiles

  摘要：

  Cationic amphiphiles 1a-1c, with monosaccharide at the omega-position of the hydrocarbon tails, were synthesized by utilization of Schmidt's trichloroacetimidate procedure for the glycosylation step acid application of the commercially available 3,5-dihydroxybenzyl alcohol as a scaffold for the attachment of double hydrocarbon tails. Application of the Zemplen condition for O-deacetylation in the presence of base-sensitive benzyl bromide was found to be efficient. The synthetic route provides an entry for the synthesis of versatile quaternary ammonium amphiphiles having the cell targeting glycosyl ligands. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01558-0
• 作为产物：
  描述：

  2,3,4,5-tetra-O-acetyl-D-glucopyranose 在 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 4-Angstroem MS 作用下， 反应 3.5h， 生成 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(12-iodo-dodecyloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of targetable cationic amphiphiles

  摘要：

  Cationic amphiphiles 1a-1c, with monosaccharide at the omega-position of the hydrocarbon tails, were synthesized by utilization of Schmidt's trichloroacetimidate procedure for the glycosylation step acid application of the commercially available 3,5-dihydroxybenzyl alcohol as a scaffold for the attachment of double hydrocarbon tails. Application of the Zemplen condition for O-deacetylation in the presence of base-sensitive benzyl bromide was found to be efficient. The synthetic route provides an entry for the synthesis of versatile quaternary ammonium amphiphiles having the cell targeting glycosyl ligands. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01558-0