Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[6-(12-hydroxy-dodecylcarbamoyloxy)-hexyloxy]-tetrahydro-pyran-4-yl ester | 393565-22-5

• 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,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[6-(12-hydroxy-dodecylcarbamoyloxy)-hexyloxy]-tetrahydro-pyran-4-yl ester
• CAS: 393565-22-5
• 化学式: C₃₃H₅₇NO₁₃
• 分子量: 675.814
• InChiKey: FSPORAIYUZRUDO-UNKWROQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  47.0
• 可旋转键数：
  25.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  182.22
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N,N'-羰基二咪唑 、 Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[6-(12-hydroxy-dodecylcarbamoyloxy)-hexyloxy]-tetrahydro-pyran-4-yl ester 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以89%的产率得到Imidazole-1-carboxylic acid 12-[6-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexyloxycarbonylamino]-dodecyl ester
  参考文献：
  名称：

  Synthesis of galactosyl compounds for targeted gene delivery

  摘要：

  Cell-specific DNA delivery offers a great potential for targeted gene therapy. Toward this end, we have synthesized a series of compounds carrying galactose residues as a targeting ligand for asialoglycoprotein receptors of hepatocytes and primary amine groups as a functional domain for DNA binding. Biological activity of these galactosyl compounds in DNA delivery was evaluated in HepG2 and BL-6 cells and compared with respect to the number of galactose residues as well as primary amine groups in each molecule. Transfection. experiments using a firefly luciferase gene as a reporter revealed that compounds with multivalent binding properties were more active in DNA delivery. An optimal transfection activity in HepG2 cells requires seven primary amine groups and a minimum of two galactose residues in each molecule. The transfection activity of compounds carrying multi-galactose residues can be inhibited by asialofetuin, a natural substrate for asialoglycoprotein receptors of hepatocytes, suggesting that gene transfer by these galactosyl compounds is asialoglycoprotein receptor-mediated. These results provide direct evidence in support of our new strategy for the use of small and synthetic compounds for cell specific and targeted gene delivery. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00203-6
• 作为产物：
  描述：

  (12-bromododecyloxy)(tert-butyl)dimethylsilane 在 sodium azide 、 四丁基氟化铵 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 27.0h， 生成 Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[6-(12-hydroxy-dodecylcarbamoyloxy)-hexyloxy]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of galactosyl compounds for targeted gene delivery

  摘要：

  Cell-specific DNA delivery offers a great potential for targeted gene therapy. Toward this end, we have synthesized a series of compounds carrying galactose residues as a targeting ligand for asialoglycoprotein receptors of hepatocytes and primary amine groups as a functional domain for DNA binding. Biological activity of these galactosyl compounds in DNA delivery was evaluated in HepG2 and BL-6 cells and compared with respect to the number of galactose residues as well as primary amine groups in each molecule. Transfection. experiments using a firefly luciferase gene as a reporter revealed that compounds with multivalent binding properties were more active in DNA delivery. An optimal transfection activity in HepG2 cells requires seven primary amine groups and a minimum of two galactose residues in each molecule. The transfection activity of compounds carrying multi-galactose residues can be inhibited by asialofetuin, a natural substrate for asialoglycoprotein receptors of hepatocytes, suggesting that gene transfer by these galactosyl compounds is asialoglycoprotein receptor-mediated. These results provide direct evidence in support of our new strategy for the use of small and synthetic compounds for cell specific and targeted gene delivery. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00203-6