1,2:3,4-di-O-ethylidene-α-L-fucose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1,2:3,4-di-O-ethylidene-α-L-fucose
• 英文别名: (1R,2S,6S,8S,9R)-4,8,11-trimethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: IIJVTDHWNNVLSO-VATOXPBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酸乙烯酯 、 L(-)岩藻糖 在 碘 作用下， 反应 2.0h， 生成 1,2:3,4-di-O-ethylidene-α-L-fucose
  参考文献：
  名称：

  Tandem Acetalation−Acetylation of Sugars and Related Derivatives with Enolacetates under Solvent-Free Conditions

  摘要：

  [GRAPHICS]Molecular iodine catalyzes acetalation and acetylation of reducing sugars and sugar glycosides with stoichiometric amounts of enol acetates under solvent-free conditions, thereby facilitating the synthesis of various types of orthogonally protected sugar derivatives in short time and good yields. The outcome of the reaction can be controlled by variation in temperature. Thus at lower temperature, it is possible to obtain the acetonide acetate as a single product whereas peracetate is the major product at higher temperature.

  DOI：

  10.1021/jo070363i

文献信息

• Tandem Acetalation−Acetylation of Sugars and Related Derivatives with Enolacetates under Solvent-Free Conditions
  作者：Debaraj Mukherjee、Bhahwal Ali Shah、Pankaj Gupta、Subhash Chandra Taneja

  DOI：10.1021/jo070363i

  日期：2007.11.1

  [GRAPHICS]Molecular iodine catalyzes acetalation and acetylation of reducing sugars and sugar glycosides with stoichiometric amounts of enol acetates under solvent-free conditions, thereby facilitating the synthesis of various types of orthogonally protected sugar derivatives in short time and good yields. The outcome of the reaction can be controlled by variation in temperature. Thus at lower temperature, it is possible to obtain the acetonide acetate as a single product whereas peracetate is the major product at higher temperature.