(2R,4R,5R,6R)-4-acetyl-5-hydroxy-2-phenyl-6-vinyl-[1,3]dioxane | 205934-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2R,4R,5R,6R)-4-acetyl-5-hydroxy-2-phenyl-6-vinyl-[1,3]dioxane
• 英文别名: 1-[(2R,4R,5R,6R)-6-ethenyl-5-hydroxy-2-phenyl-1,3-dioxan-4-yl]ethanone
• CAS: 205934-65-2
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: WQTOFEOQNJHVCH-YIYPIFLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,4R,5R,6R)-4-acetyl-5-hydroxy-2-phenyl-6-vinyl-[1,3]dioxane 在 咪唑 、 正丁基锂 、 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.5h， 生成 (2R,4R,5R,6R)-6-ethenyl-5-hydroxy-4-[(1S)-1-hydroxy-1-(2,5-dimethoxyphenyl)-ethyl]-2-phenyl-[1,3]dioxane
  参考文献：
  名称：

  Studies on the Synthesis of the C-Glycosidic Part of Nogalamycin, Part 2

  摘要：

  The stereochemistry of the addition of metalloaryls 11w-z to the methyl ketones 10a-e was studied in connection with the construction of the hogalamycin C-glycoside. Excellent selectivities towards the (S)-isomer 13a were observed in the beta-chelate model B in the reaction of the benzyl ethers 10a with the cerium reagent 11y and the titanium reagent 11z or the alcohol 10c with the lithium compound 11w. A moderate 3:1 selectivity in favor of the desired (R)-isomer was observed in the reaction of the silyl ether 10d with 11w. A reversal of the addition sequence (reaction of 15a with MeMgI) led exclusively to 13a whereas the alcohol 15c gave a 5:3 mixture of 12c:13c.

  DOI：

  10.1080/07328309808002321
• 作为产物：
  描述：

  (2S,3R,4R)-3-(4-Methoxy-benzyloxy)-hex-5-ene-1,2,4-triol 在 重铬酸吡啶 、 乙酸酐 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 26.0h， 生成 (2R,4R,5R,6R)-4-acetyl-5-hydroxy-2-phenyl-6-vinyl-[1,3]dioxane
  参考文献：
  名称：

  Studies on the Synthesis of the C-Glycosidic Part of Nogalamycin, Part 2

  摘要：

  The stereochemistry of the addition of metalloaryls 11w-z to the methyl ketones 10a-e was studied in connection with the construction of the hogalamycin C-glycoside. Excellent selectivities towards the (S)-isomer 13a were observed in the beta-chelate model B in the reaction of the benzyl ethers 10a with the cerium reagent 11y and the titanium reagent 11z or the alcohol 10c with the lithium compound 11w. A moderate 3:1 selectivity in favor of the desired (R)-isomer was observed in the reaction of the silyl ether 10d with 11w. A reversal of the addition sequence (reaction of 15a with MeMgI) led exclusively to 13a whereas the alcohol 15c gave a 5:3 mixture of 12c:13c.

  DOI：

  10.1080/07328309808002321