((4R)-formyl-(2R)-phenyl-(6R)-vinyl-[1,3]dioxane-(5S)-yl)methylcarbamic acid methyl ester | 205868-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: ((4R)-formyl-(2R)-phenyl-(6R)-vinyl-[1,3]dioxane-(5S)-yl)methylcarbamic acid methyl ester
• 英文别名: methyl N-[(2R,4R,5S,6R)-4-ethenyl-6-formyl-2-phenyl-1,3-dioxan-5-yl]-N-methylcarbamate
• CAS: 205868-33-3
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: MCCFSAZNFAQULF-CBBWQLFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((4R)-formyl-(2R)-phenyl-(6R)-vinyl-[1,3]dioxane-(5S)-yl)methylcarbamic acid methyl ester 在 盐酸 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 正丁基锂 、 乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (2S,3R,4S,5R)-2-(2,5-Dimethoxy-phenyl)-4-dimethylamino-hept-6-ene-2,3,5-triol; hydrochloride
  参考文献：
  名称：

  Studies on the Synthesis of the C-Glycosidic Part of Nogalamycin, Part 3

  摘要：

  The addition of the metalated 1,4-dimethoxybenzenes 17a-c to the methyl ketone 14 was investigated in connection with the construction of the C-glycosidic part of nogalamycin. In most reactions, a selectivity towards the undesired Q-isomer 16a was observed, However, the reaction of the lithiated aromate 17c with 14 at low temperatures in THF favored the formation of the desired (R)-alcohol 15a (15a:16a = 4.8:1) in accordance with the chelate model A. The selectivity was considerably enhanced in the addition of the more hindered lithiated naphthalene 18 yielding the (R)-isomer 15b exclusively. Reduction of 15b afforded the dimethylamino compound 19b, a direct precursor of the CDEF-ring system of nogalamycin.

  DOI：

  10.1080/07328309808002322
• 作为产物：
  描述：

  在 水 、 碘 、 碳酸氢钠 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 sodium iodide 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 丁酮 为溶剂， 反应 66.0h， 生成 ((4R)-formyl-(2R)-phenyl-(6R)-vinyl-[1,3]dioxane-(5S)-yl)methylcarbamic acid methyl ester
  参考文献：
  名称：

  Studies on the Synthesis of the C-Glycosidic Part of Nogalamycin, Part 3

  摘要：

  The addition of the metalated 1,4-dimethoxybenzenes 17a-c to the methyl ketone 14 was investigated in connection with the construction of the C-glycosidic part of nogalamycin. In most reactions, a selectivity towards the undesired Q-isomer 16a was observed, However, the reaction of the lithiated aromate 17c with 14 at low temperatures in THF favored the formation of the desired (R)-alcohol 15a (15a:16a = 4.8:1) in accordance with the chelate model A. The selectivity was considerably enhanced in the addition of the more hindered lithiated naphthalene 18 yielding the (R)-isomer 15b exclusively. Reduction of 15b afforded the dimethylamino compound 19b, a direct precursor of the CDEF-ring system of nogalamycin.

  DOI：

  10.1080/07328309808002322