4,6-O-methoxyethylidenesucrose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,6-O-methoxyethylidenesucrose
• 英文别名: Sucrose 4,6-Methyl Orthoester；(4aR,6R,7R,8R,8aS)-6-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-2-methoxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• 化学式: C₁₅H₂₆O₁₂
• 分子量: 398.364
• InChiKey: GPHQAYOJGDRUCF-NPKNDJINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  177
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4,6-O-methoxyethylidenesucrose 在 吡啶 作用下， 以84%的产率得到Acetic acid (2S,3S,4R,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-((4aR,6R,7R,8S,8aR)-7,8-diacetoxy-2-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Further examples of orthoesterification under kinetically controlled conditions application to the selective acylation of sucrose, maltose and α,α-trehalose

  摘要：

  Orthoesterification of sucrose with 1,1-dimethoxyethene under kinetic control gave 4,6-O-methoxyethylidenesucrose in 77% crude yield. Similar orthoesterification of maltose led essentially after acetylation to 1,2,3,6,2',3'-hexa-O-acetyl-4'-6'-O-methoxyethylidenemaltose. Analogous treatment of alpha,alpha-trehalose gave 2,3,2',3'-tetra-O-acetyl-4,6:4',6'-di-O-methoxyethylidene-alpha,alpha-trehalose in 47% yield. The acid-catalyzed opening of these orthoesters was studied, and these reactions were shown to give disaccharides selectively protected by acetyl groups. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00208-5
• 作为产物：
  描述：

  1,1-二甲氧基乙烯 、 蔗糖 在 Sikkon 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以77%的产率得到4,6-O-methoxyethylidenesucrose
  参考文献：
  名称：

  Further examples of orthoesterification under kinetically controlled conditions application to the selective acylation of sucrose, maltose and α,α-trehalose

  摘要：

  Orthoesterification of sucrose with 1,1-dimethoxyethene under kinetic control gave 4,6-O-methoxyethylidenesucrose in 77% crude yield. Similar orthoesterification of maltose led essentially after acetylation to 1,2,3,6,2',3'-hexa-O-acetyl-4'-6'-O-methoxyethylidenemaltose. Analogous treatment of alpha,alpha-trehalose gave 2,3,2',3'-tetra-O-acetyl-4,6:4',6'-di-O-methoxyethylidene-alpha,alpha-trehalose in 47% yield. The acid-catalyzed opening of these orthoesters was studied, and these reactions were shown to give disaccharides selectively protected by acetyl groups. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00208-5

文献信息

• Further examples of orthoesterification under kinetically controlled conditions application to the selective acylation of sucrose, maltose and α,α-trehalose
  作者：Mohamed Bouchra、Jacques Gelas

  DOI：10.1016/s0008-6215(97)00208-5

  日期：1997.12

  Orthoesterification of sucrose with 1,1-dimethoxyethene under kinetic control gave 4,6-O-methoxyethylidenesucrose in 77% crude yield. Similar orthoesterification of maltose led essentially after acetylation to 1,2,3,6,2',3'-hexa-O-acetyl-4'-6'-O-methoxyethylidenemaltose. Analogous treatment of alpha,alpha-trehalose gave 2,3,2',3'-tetra-O-acetyl-4,6:4',6'-di-O-methoxyethylidene-alpha,alpha-trehalose in 47% yield. The acid-catalyzed opening of these orthoesters was studied, and these reactions were shown to give disaccharides selectively protected by acetyl groups. (C) 1998 Elsevier Science Ltd.