4-O-Benzyl-3-O-(methoxymethyl)-D-glucal | 137792-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-O-Benzyl-3-O-(methoxymethyl)-D-glucal
• 英文别名: [(2R,3S,4R)-4-(methoxymethoxy)-3-phenylmethoxy-3,4-dihydro-2H-pyran-2-yl]methanol
• CAS: 137792-86-0
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: NQKWAEXPRABFQE-KFWWJZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-O-Benzyl-3-O-(methoxymethyl)-D-glucal 在 咪唑 、 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-O-Benzyl-6-O-(tert-butyldimethylsilyl)-1,2,7,8-tetradeoxy-3-O-(methoxymethyl)-L-galacto-D-altro-octa-1,7-dieno-1,5-pyranose
  参考文献：
  名称：

  Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes

  摘要：

  Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group. Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on the lengths of the olefinic appendages. Hydrolysis of the anomeric centers of the [2.2.1] structures leads spontaneously to cyclopentane derivatives. However, with [2.2.2] structures, the hemiacetal intermediates are stable in bicyclic forms but are opened readily upon mcerpatolysis with propane dithiol to give cyclohexane derivatives.

  DOI：

  10.1021/jo00028a033
• 作为产物：
  描述：

  D-葡萄烯糖 在 吡啶 、 咪唑 、 四丁基氟化铵 、 四丁基碘化铵 、 potassium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.58h， 生成 4-O-Benzyl-3-O-(methoxymethyl)-D-glucal
  参考文献：
  名称：

  Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes

  摘要：

  Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group. Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on the lengths of the olefinic appendages. Hydrolysis of the anomeric centers of the [2.2.1] structures leads spontaneously to cyclopentane derivatives. However, with [2.2.2] structures, the hemiacetal intermediates are stable in bicyclic forms but are opened readily upon mcerpatolysis with propane dithiol to give cyclohexane derivatives.

  DOI：

  10.1021/jo00028a033

文献信息

• Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes
  作者：R. A. Alonso、G. D. Vite、R. E. McDevitt、B. Fraser-Reid

  DOI：10.1021/jo00028a033

  日期：1992.1

  Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group. Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on the lengths of the olefinic appendages. Hydrolysis of the anomeric centers of the [2.2.1] structures leads spontaneously to cyclopentane derivatives. However, with [2.2.2] structures, the hemiacetal intermediates are stable in bicyclic forms but are opened readily upon mcerpatolysis with propane dithiol to give cyclohexane derivatives.