methyl 6-O-methacryloyl-α-D-mannopyranoside | 870481-73-5

• 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-mannopyranoside
• 英文别名: [(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl 2-methylprop-2-enoate
• CAS: 870481-73-5
• 化学式: C₁₁H₁₈O₇
• 分子量: 262.26
• InChiKey: KYWKLXMTGOXSRA-ABCHNEDTSA-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

• 作为产物：
  描述：

  甲基丙烯酸乙烯酯 、 甲基-D-丙噻 在 Novozym 435 、 2,6-二叔丁基-4-甲基苯酚 作用下， 以 乙腈 为溶剂， 反应 168.0h， 以48%的产率得到methyl 6-O-methacryloyl-α-D-mannopyranoside
  参考文献：
  名称：

  Well-Defined Diblock Glycopolymers from RAFT Polymerization in Homogeneous Aqueous Medium

  摘要：

  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.

  DOI：

  10.1021/ma051310a

文献信息

• 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.