2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-phenyl(diisopropyl)silyl-D-glucitol | 222408-86-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-phenyl(diisopropyl)silyl-D-glucitol
• 英文别名: [(2R,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]methyl-phenyl-di(propan-2-yl)silane
• CAS: 222408-86-8
• 化学式: C₃₉H₄₈O₄Si
• 分子量: 608.893
• InChiKey: RHRDIYKOOQQCOU-UCBPDFRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.32
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-phenyl(diisopropyl)silyl-D-glucitol 在 叔丁基过氧化氢 、 cesium hydroxide 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 2,5-anhydro-3,4,6-tri-O-benzyl-D-glucitol
  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：

  2,3,5-tri-O-benzyl-L-arabinofuranose 在 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-phenyl(diisopropyl)silyl-D-glucitol
  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

文献信息

• Preparation of 2,5-Anhydrohexitols (Part I). Silicon-Directed Stereocontrolled Cyclization
  作者：Floris L. van Delft、A. Rob、P.M. Valentijn、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1080/07328309908543989

  日期：1999.1.1

  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.