methyl 6-O-methacryloyl-α-D-glucopyranoside | 121469-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-methacryloyl-α-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl 2-methylprop-2-enoate
• CAS: 121469-97-4
• 化学式: C₁₁H₁₈O₇
• 分子量: 262.26
• InChiKey: KYWKLXMTGOXSRA-DZEUPHNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 6-O-methacryloyl-α-D-glucopyranoside 在 吡啶 作用下， 生成 methyl 2,3,4-tri-O-acetyl-6-O-methacryloyl-α-D-glucopyranoside
  参考文献：
  名称：

  Bourhim, Abdellatif; Czernecki, Stanislas; Krausz, Pierre, Journal of Carbohydrate Chemistry, 1993, vol. 12, # 7, p. 853 - 863

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基丙烯酸三氟乙酯 、 alpha-甲基葡萄糖甙 在 proteinase N 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 以33%的产率得到methyl 6-O-methacryloyl-α-D-glucopyranoside
  参考文献：
  名称：

  Proteinase N-catalysed regioselective esterification of sucrose and other mono- and disaccharides

  摘要：

  Crude Proteinase N was used as catalyst for the synthesis of carbohydrate (in particular sucrose) esters by transesterification of activated esters in organic solvents. Polymerisable or amphiphilic sucrose esters (methacrylates and laurates) were obtained regioselectively in good yields. The influence of the reaction parameters (temperature, pH, solvent, chain length, solid support) on the reaction rate, yield and selectivity was studied. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00424-4

文献信息

• Synthesis, characterization and fluorescent properties of water-soluble glycopolymer bearing curcumin pendant residues
  作者：Haisong Zhang、Meng Yu、Hailei Zhang、Libin Bai、Yonggang Wu、Sujuan Wang、Xinwu Ba

  DOI：10.1080/09168451.2016.1171696

  日期：2016.8.2

  aqueous solubility of curcumin is enhanced by means of modification with the carbohydrate units. Polymerization of the curcumin-containing monomer with carbohydrate-containing monomer gives the water-soluble glycopolymer bearing curcumin pendant residues. The obtained copolymers (P1 and P2) having desirable water solubility were well-characterized by infrared spectroscopy (IR), nuclear magnetic resonance

  姜黄素是一种潜在的天然抗癌药物，由于水溶性差，口服生物利用度低。姜黄素的水溶性通过碳水化合物单元的修饰得以增强。含姜黄素的单体与含碳水化合物的单体的聚合得到带有姜黄素侧基的水溶性糖聚合物。通过红外光谱（IR），核磁共振（NMR），凝胶渗透色谱法（GPC），UV-Vis吸收光谱法和光致发光光谱法很好地表征了具有所需水溶性的所得共聚物（P1和P2）。根据质子NMR结果计算，摩尔比为1：6（姜黄素/碳水化合物）的共聚物P2与原始姜黄素相比具有相似的抗癌活性，
• 10.1021/ma049129
  作者：Albertin, Luca、Stenzel, Martina、Barner-Kowollik, Christopher、Foster, L. John R.、Davis, Thomas P.

  DOI：10.1021/ma049129

  日期：——
• Well-Defined Diblock Glycopolymers from RAFT Polymerization in Homogeneous Aqueous Medium
  作者：Luca Albertin、Martina H. Stenzel、Christopher Barner-Kowollik、L. John R. Foster、Thomas P. Davis

  DOI：10.1021/ma051310a

  日期：2005.11.1

  Reversible addition-fragmentation chain transfer polymerization was applied to the synthesis of well-defined diblock glycopolymers carrying different cyclic carbohydrates on the two blocks. The macroRAFT agents poly(methyl 6-O-methaeryloyl-alpha-D-glucoside) dithiobenzoate and poly(2-methacryloxyethyl glucoside) dithiobenzoate were prepared by RAFT polymerization of the corresponding glycomonomers with (4-cyanopentanoic acid)-4-dithiobenzoate as the chain transfer agent. The reactions were stopped around 85% conversion in order to preserve the highest possible end-of-chain-functionality and the glycopolymers were isolated by precipitation in methanol. Chain extension with 2-methacryloxyethyl glucoside and methyl 6-O-methacryloyl-alpha-D-mannoside afforded poly(methyl 6-O-methacryloyl-alpha-D-glucoside-block-2-methacryloxyethyl glucoside) and poly(2-methacryloxyethyl glucoside-block-methyl 6-O-methacryloyl-alpha-D-mannoside), respectively, having a predetermined molecular weight and narrow polydispersity (PDI <= 1.20). The structure of the prepared polymers was confirmed by proton and carbon NMR and their thermal properties investigated via DSC.
• BERAUD, PIERRE;BOURHIM, ABDELATIF;CZERNECKI, STANISLAS;KRAUSZ, PIERRE, TETRAHEDRON LETT., 30,(1989) N 3, C. 325-326
  作者：BERAUD, PIERRE、BOURHIM, ABDELATIF、CZERNECKI, STANISLAS、KRAUSZ, PIERRE

  DOI：——

  日期：——