sucrose 1'-O-crotonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sucrose 1'-O-crotonate
• 英文别名: [(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl (E)-but-2-enoate
• 化学式: C₁₆H₂₆O₁₂
• 分子量: 410.375
• InChiKey: CQHDJYVLSLTWMU-PFDGOMGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2,2,2-三氟乙基巴豆酸酯 、 蔗糖 在 proteinase N 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以6%的产率得到sucrose 1'-O-crotonate
  参考文献：
  名称：

  Proteinase N-catalysed transesterifications in DMSO–water and DMF–water: preparation of sucrose monomethacrylate

  摘要：

  The selective acylation of sucrose was catalysed by proteinase N (from Bacillus subtilis) in DMF suspensions, providing 1'-monoesters, and notably, methacryloyl esters. Presence of water up to 7% (vol.) led to faster reactions. Alternatively, a slurry of the enzyme with a minimum volume of DMSO could also be used, despite its ability to denature enzymes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00452-4

文献信息

• Proteinase N-catalysed regioselective esterification of sucrose and other mono- and disaccharides
  作者：Pierre Potier、Alain Bouchu、Juliette Gagnaire、Yves Queneau

  DOI：10.1016/s0957-4166(01)00424-4

  日期：2001.9

  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.
• Proteinase N-catalysed transesterifications in DMSO–water and DMF–water: preparation of sucrose monomethacrylate
  作者：Pierre Potier、Alain Bouchu、Gérard Descotes、Yves Queneau

  DOI：10.1016/s0040-4039(00)00452-4

  日期：2000.5

  The selective acylation of sucrose was catalysed by proteinase N (from Bacillus subtilis) in DMF suspensions, providing 1'-monoesters, and notably, methacryloyl esters. Presence of water up to 7% (vol.) led to faster reactions. Alternatively, a slurry of the enzyme with a minimum volume of DMSO could also be used, despite its ability to denature enzymes. (C) 2000 Elsevier Science Ltd. All rights reserved.