3-(12,12,13,13,14,14,15,15,16,16,17,17,17-tridecafluoroheptadecanoyl)-2,2-dimethyl-4(R)-thiazolidine-4-carboxylic acid | 1016561-25-3

• 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: 3-(12,12,13,13,14,14,15,15,16,16,17,17,17-tridecafluoroheptadecanoyl)-2,2-dimethyl-4(R)-thiazolidine-4-carboxylic acid
• 英文别名: (4R)-2,2-dimethyl-3-(12,12,13,13,14,14,15,15,16,16,17,17,17-tridecafluoroheptadecanoyl)-1,3-thiazolidine-4-carboxylic acid
• CAS: 1016561-25-3
• 化学式: C₂₃H₃₀F₁₃NO₃S
• 分子量: 647.541
• InChiKey: LEMJMMLTVBLXCD-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  11-(全氟己基)十一烷酰氯 、 (4R)-2,2-二甲基-4-噻唑烷甲酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以1.13 g的产率得到3-(12,12,13,13,14,14,15,15,16,16,17,17,17-tridecafluoroheptadecanoyl)-2,2-dimethyl-4(R)-thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  An efficient mixed solid–liquid phase synthesis of a heterobifunctional amphiphilic PEG–NH2 derivative and its conjugation to folic acid

  摘要：

  A very efficient, versatile as well as simple to perform procedure was developed in order to prepare a heterobifunctional amphiphilic PEG-NH(2) derivative which can be used for conjugation to a targeting ligand (such as folic acid). This method proceeds by a mixed solid-liquid phase strategy using a TentaGel (R) PAP resin, a copolymer consisting of a polystyrene matrix on which a PEG (M(w) 3400 Da) terminated by an amino function has been grafted. Solid phase chemistry was used for the conjugation of a highly hydrophobic moiety. After release from the resin, the amphiphilic PEG-OH conjugate was converted into its corresponding amphiphilic PEG-NH(2) derivative (four steps in 77% overall yields). This procedure allowed the preparation of similar to 330 mg batches. This derivative was then coupled to folic acid, a ligand that is used for the targeting of drug (gene) carrier and delivery systems to cells over-expressing the folate receptor. The low and high molecular weight of folic acid and its amphiphilic PEG-folate conjugate, respectively, allowed easy purification by dialysis and led to the targeted compound with high recovery. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.027

文献信息

• An efficient mixed solid–liquid phase synthesis of a heterobifunctional amphiphilic PEG–NH2 derivative and its conjugation to folic acid
  作者：Loïc Le Gourriérec、Christophe Di Giorgio、Jacques Greiner、Pierre Vierling

  DOI：10.1016/j.tet.2007.12.027

  日期：2008.2

  A very efficient, versatile as well as simple to perform procedure was developed in order to prepare a heterobifunctional amphiphilic PEG-NH(2) derivative which can be used for conjugation to a targeting ligand (such as folic acid). This method proceeds by a mixed solid-liquid phase strategy using a TentaGel (R) PAP resin, a copolymer consisting of a polystyrene matrix on which a PEG (M(w) 3400 Da) terminated by an amino function has been grafted. Solid phase chemistry was used for the conjugation of a highly hydrophobic moiety. After release from the resin, the amphiphilic PEG-OH conjugate was converted into its corresponding amphiphilic PEG-NH(2) derivative (four steps in 77% overall yields). This procedure allowed the preparation of similar to 330 mg batches. This derivative was then coupled to folic acid, a ligand that is used for the targeting of drug (gene) carrier and delivery systems to cells over-expressing the folate receptor. The low and high molecular weight of folic acid and its amphiphilic PEG-folate conjugate, respectively, allowed easy purification by dialysis and led to the targeted compound with high recovery. (C) 2007 Elsevier Ltd. All rights reserved.