6-O-methacryloyl-D-galactose | 19179-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-methacryloyl-D-galactose
• 英文别名: 6-O-methacryloylgalactopyranose；[(2R,3R,4S,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 2-methylprop-2-enoate
• CAS: 19179-68-1
• 化学式: C₁₀H₁₆O₇
• 分子量: 248.233
• InChiKey: WCIOMCVCZCOSFM-UTABRTIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-O-methacryloyl-1,2:3,4-di-O-isopropylidene-D-galactopyranose 在 甲酸 、 4-甲氧基苯酚 作用下， 以 水 为溶剂， 反应 20.0h， 生成 6-O-methacryloyl-D-galactose
  参考文献：
  名称：

  Synthesis of Water-Soluble Polymeric Prodrugs Possessing 4-Methylcatechol Derivatives by Mechanochemical Solid-State Copolymerization and Nature of Drug Release.

  摘要：

  在本研究中，我们通过机械化学固态共聚合成了含有4-甲基儿茶酚（4MC）衍生物侧链的水溶性聚合物前药。选择1-苯甲酰基-4-甲基儿茶酚（Bz4MC）作为4MC的模型化合物，并合成了其甲基丙烯酰基衍生物（1）。还合成了水溶性单体6-O-甲基丙烯酰基-D-半乳糖（2）。通过1和2的机械化学固态共聚合，获得了具有Bz4MC侧链的水溶性聚合物前药。1和2的机械化学共聚合完全进行，生成的聚合物前药具有狭窄的分子量分布。三种组成不同的聚合物前药在体外进行了水解。这些聚合物前药的水解完全进行。水解速率常数随聚合物前药中1的摩尔分数增加而减小。表明水解速率常数可以通过聚合物前药的组成、1的摩尔分数来控制。

  DOI：

  10.1248/cpb.50.1434

文献信息

• Synthesis of Water-Soluble Polymeric Prodrugs Possessing 4-Methylcatechol Derivatives by Mechanochemical Solid-State Copolymerization and Nature of Drug Release.
  作者：Shin-ichi Kondo、Yasushi Sasai、Masayuki Kuzuya、Shoei Furukawa

  DOI：10.1248/cpb.50.1434

  日期：——

  In this study we synthesized the water-soluble polymeric prodrugs possessing a 4-methylcatechol (4MC) derivative as a side chain by mechanochemical solid-state copolymerization. 1-Benzoyl-4-methylcatechol (Bz4MC) was selected as a model compound of 4MC, and its methacryloyl derivative (1) was synthesized. 6-O-Methacryloyl-D-galactose (2) was also prepared as a water-soluble monomer. The mechanochemical solid-state copolymerization of 1 and 2 was carried out to obtain the water-soluble polymeric prodrug possessing the Bz4MC as a side chain. The mechanochemical copolymerization of 1 and 2 proceeded to completion, and the polymeric prodrug produced possessed a narrow molecular weight distribution. Three kinds of polymeric prodrugs, whose compositions were different from one another, were hydrolyzed in vitro. The hydrolysis of these polymeric prodrugs proceeded to completion. The rate constants of hydrolysis decreased with increasing the mole fraction of 1 in polymeric prodrug. It was suggested that the rate constant of hydrolysis could be controlled by the composition, the mole fraction of 1 in the polymeric prodrug.

  在本研究中，我们通过机械化学固态共聚合成了含有4-甲基儿茶酚（4MC）衍生物侧链的水溶性聚合物前药。选择1-苯甲酰基-4-甲基儿茶酚（Bz4MC）作为4MC的模型化合物，并合成了其甲基丙烯酰基衍生物（1）。还合成了水溶性单体6-O-甲基丙烯酰基-D-半乳糖（2）。通过1和2的机械化学固态共聚合，获得了具有Bz4MC侧链的水溶性聚合物前药。1和2的机械化学共聚合完全进行，生成的聚合物前药具有狭窄的分子量分布。三种组成不同的聚合物前药在体外进行了水解。这些聚合物前药的水解完全进行。水解速率常数随聚合物前药中1的摩尔分数增加而减小。表明水解速率常数可以通过聚合物前药的组成、1的摩尔分数来控制。