2,5-anhydro-3,4-di-O-benzyl-D-altritol | 222555-98-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-3,4-di-O-benzyl-D-altritol
• CAS: 222555-98-8
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: GCCFBDFJFARWGD-WTGUMLROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3,4-di-O-benzyl-D-altritol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以90%的产率得到2,5-anhydro-D-altritol
  参考文献：
  名称：

  Preparation of 2,5-Anhydrohexitols (Part I). Silicon-Directed Stereocontrolled Cyclization

  摘要：

  Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3. Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.

  DOI：

  10.1080/07328309908543989
• 作为产物：
  描述：

  3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-O-isopropylidene-D-altritol 在 过氧乙酸 、 硫酸 、 sodium acetate 、 溶剂黄146 、 potassium bromide 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 20.0h， 生成 2,5-anhydro-3,4-di-O-benzyl-D-altritol
  参考文献：
  名称：

  Preparation of 2,5-Anhydrohexitols (Part I). Silicon-Directed Stereocontrolled Cyclization

  摘要：

  Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3. Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.

  DOI：

  10.1080/07328309908543989