(2R,4R,5S,6R)-5-Benzyloxy-2-phenyl-6-vinyl-[1,3]dioxane-4-carbaldehyde | 205816-25-7

• 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: (2R,4R,5S,6R)-5-Benzyloxy-2-phenyl-6-vinyl-[1,3]dioxane-4-carbaldehyde
• CAS: 205816-25-7
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: QBTDOPUHOGVFMH-FUMNGEBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,4R,5S,6R)-5-Benzyloxy-2-phenyl-6-vinyl-[1,3]dioxane-4-carbaldehyde 在 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 1-((2R,4R,5S,6R)-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)ethanone
  参考文献：
  名称：

  Studies on the Synthesis of the C-Glycosidic Part of Nogalamycin, Part 1

  摘要：

  Studies aimed at the construction of the C-glycosidic part of nogalamycin (1) and menogarol (2) are described. The stereochemistry of the addition of aryl lithiums to 4-acetyl-1,3-dioxolane 16, prepared from D-glucose via 10a-15, was studied. The major isomers were the Q-isomers 17a and 17b as shown by X-ray analysis of 17a with the unnatural configuration. The adduct 17a was further converted to the anomeric naphthoquinones 22a and 22b by acetal cleavage, ozonolysis, acetalization and Diels-Alder reaction with 1-methoxybutadiene.

  DOI：

  10.1080/07328309808002320
• 作为产物：
  描述：

  (2R,4S,5S,6R)-(5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxan-4-yl)-methanol 在 chromium trioxide-pyridine complex 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以68%的产率得到(2R,4R,5S,6R)-5-Benzyloxy-2-phenyl-6-vinyl-[1,3]dioxane-4-carbaldehyde
  参考文献：
  名称：

  Studies on the Synthesis of the C-Glycosidic Part of Nogalamycin, Part 1

  摘要：

  Studies aimed at the construction of the C-glycosidic part of nogalamycin (1) and menogarol (2) are described. The stereochemistry of the addition of aryl lithiums to 4-acetyl-1,3-dioxolane 16, prepared from D-glucose via 10a-15, was studied. The major isomers were the Q-isomers 17a and 17b as shown by X-ray analysis of 17a with the unnatural configuration. The adduct 17a was further converted to the anomeric naphthoquinones 22a and 22b by acetal cleavage, ozonolysis, acetalization and Diels-Alder reaction with 1-methoxybutadiene.

  DOI：

  10.1080/07328309808002320