methyl 3-C-acetyl-3,6-anhydro-4,5,7-tri-O-benzyl-2-deoxy-D-altro-heptonate | 1021954-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-C-acetyl-3,6-anhydro-4,5,7-tri-O-benzyl-2-deoxy-D-altro-heptonate
• CAS: 1021954-42-6
• 化学式: C₃₁H₃₄O₇
• 分子量: 518.607
• InChiKey: DJATUKZCYXUKOC-RJIGRWNCSA-N

物化性质

• 沸点：
  625.9±55.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  甲醇 、 在 过碘酸 作用下， 反应 2.0h， 生成 methyl 3-C-acetyl-3,6-anhydro-4,5,7-tri-O-benzyl-2-deoxy-D-altro-heptonate 、 methyl 3-C-acetyl-3,6-anhydro-4,5,7-tri-O-benzyl-2-deoxy-D-allo-heptonate
  参考文献：
  名称：

  Stereocontrolled Photocyclization of 1,2-Diketones: Application of a 1,3-Acetyl Group Transfer Methodology to Carbohydrates

  摘要：

  Photolysis of 1-glycosyl-2,3-butanodione derivatives using visible light is a mild and selective procedure for the synthesis of chiral 1-hydroxy-1-methyl-5-oxaspiro[3.5]nonan-2-one carbohydrate derivatives. The results strongly suggest that stereocontrol of the cyclization is dependent on conformational and stereoelectronic factors. Further oxidative opening, of the 1-hydroxy-1-methyl-2-cyclobutanone moiety affords new C-ketoside derivatives either in C- and O-glycoside series. This tandem two-step process could be considered to be a stereocontrolled 1,3-transference of an acetyl group, and it can be applied either to pyranose and furanose models.

  DOI：

  10.1021/jo702663w