4-(β-glucosyloxy)butyl acrylate | 1357081-06-1

• 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: 4-(β-glucosyloxy)butyl acrylate
• 英文别名: 4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl prop-2-enoate
• CAS: 1357081-06-1
• 化学式: C₁₃H₂₂O₈
• 分子量: 306.313
• InChiKey: PJSLJOXGSGROTF-KABOQKQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  D-葡萄糖 、 1H-吲唑,6-溴-4-氯- 在 β-glucosidase 作用下， 以 水 为溶剂， 生成 4-(β-glucosyloxy)butyl acrylate
  参考文献：
  名称：

  Chemo-enzymatic synthesis route to poly(glucosyl-acrylates) using glucosidase from almonds

  摘要：

  β-葡萄糖苷酶从杏仁催化的糖苷化反应中获得了新型的葡萄糖基丙烯酸酯单体。糖基丙烯酸酯单体是通过 D-葡萄糖与羟基功能丙烯酸酯反应合成的：2-羟乙基丙烯酸酯（2-HEA）、2-羟乙基甲基丙烯酸酯（2-HEMA）和 4-羟丁基丙烯酸酯（4-HBA）。反应产物可分别鉴定为 2-(β-葡萄糖酰氧基)-丙烯酸乙酯、2-(β-葡萄糖酰氧基)-甲基丙烯酸乙酯和 4-(β-葡萄糖酰氧基)-丙烯酸乙酯。通过改变 2-HEA 与水的比例、水混溶助溶剂的存在和反应时间，对合成产率进行了优化。结果发现，最佳反应混合物中水的含量为 13%，2-HEA 的含量为 80%，1.4-二氧六环的含量为 7%。在这些条件下，反应 24 小时后，D-葡萄糖的最大产量为 50 wt%。酶法合成的葡萄糖基丙烯酸酯在 DMF 和水中通过自由基聚合反应成功聚合。糖基丙烯酸酯单体的糖苷键在聚合过程中得以保留。酶法合成的葡萄糖基丙烯酸酯可成功地与乙烯基单体 2-HEA、2-HEMA、甲基丙烯酸酰胺和 N-乙烯基咪唑共聚。

  DOI：

  10.1039/c3gc41115j

文献信息

• PROCESS FOR PRODUCING GLYCOSIDES OF ACRYLATE DERIVATIVES EMPLOYING SACCHARIDES AND GLYCOSIDASES
  申请人：BASF SE

  公开号：EP2598647A1

  公开（公告）日：2013-06-05
• ENZYMATIC PRODUCTION OF AN ETHYLENICALLY UNSATURATED GLYCOSIDE
  申请人：KELLER Harald

  公开号：US20120028308A1

  公开（公告）日：2012-02-02

  Ethylenically unsaturated glycosides of formula I wherein n, A, X, R 3 and R 4 have the meanings given in the description are produced by reacting an ethylenically unsaturated alcohol of formula II with a saccharide of formula III in the presence of a glycosidase, such as an amylase, cellulase, glucosidase or galactosidase, (i) at a molar ratio of ethylenically unsaturated alcohol of formula II to saccharide of formula III of from 2:1 to 30:1; (ii) in the presence of a solvent mixture of water and a water miscible organic solvent that is no primary or secondary alcohol, such as acetone, acetonitrile, t-pentanol, t-butanol, 1,4 -dioxane and tetrahydrofuran, at a weight ratio of water to organic solvent of from 0.1:1 to 9:1 ; and (iii) at a weight ratio of solvent mixture to saccharide of from 3:1 to 30:1.
• US8580538B2
  申请人：——

  公开号：US8580538B2

  公开（公告）日：2013-11-12
• [EN] PROCESS FOR PRODUCING GLYCOSIDES OF ACRYLATE DERIVATIVES EMPLOYING SACCHARIDES AND GLYCOSIDASES<br/>[FR] PROCÉDÉ DE PRODUCTION DE GLYCOSIDES DE DÉRIVÉS D'ACRYLATE EMPLOYANT DES SACCHARIDES ET DES GLYCOSIDASES
  申请人：BASF SE

  公开号：WO2012013648A1

  公开（公告）日：2012-02-02

  Ethylenically unsaturated glycosides of formula (I) wherein n, A, X, R3 and R4 have the meanings given in the description are produced by reacting an ethylenically unsaturated alcohol of formula (II) with a saccharide of formula (III) in the presence of a glycosidase, such as an amylase, cellulase, glucosidase or galactosidase, (i) at a molar ratio of ethylenically unsaturated alcohol of formula II to saccharide of formula (III) of from 2:1 to 30:1; (ii) in the presence of a solvent mixture of water and a water miscible organic solvent that is no primary or secondary alcohol, such as acetone, acetonitrile, t-pentanol, t-butanol, 1,4-dioxane and tetrahydrofuran, at a weight ratio of water to organic solvent of from 0.1 :1 to 9:1; and (iii) at a weight ratio of solvent mixture to saccharide of from 3:1 to 30:1.