{(4R)-[(1R)-hydroxy-1-(1,4,5,8-tetramethoxynaphthalene-2-yl)-ethyl]-(2R)-phenyl-(6R)-vinyl-[1,3]dioxane-(5S)-yl}methylcarbamic acid methyl ester | 205868-44-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {(4R)-[(1R)-hydroxy-1-(1,4,5,8-tetramethoxynaphthalene-2-yl)-ethyl]-(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-[(1R)-1-hydroxy-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)ethyl]-2-phenyl-1,3-dioxan-5-yl]-N-methylcarbamate
• CAS: 205868-44-6
• 化学式: C₃₁H₃₇NO₉
• 分子量: 567.636
• InChiKey: DZINFHLBGSEJAI-DEIXNTCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  105.15
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  {(4R)-[(1R)-hydroxy-1-(1,4,5,8-tetramethoxynaphthalene-2-yl)-ethyl]-(2R)-phenyl-(6R)-vinyl-[1,3]dioxane-(5S)-yl}methylcarbamic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 8.0h， 以75%的产率得到(1R)-[(5S)-(dimethylamino-(2R)-phenyl-(6R)-vinyl-[1,3]dioxane-(4R)-yl)]-1-(1,4,5,8-tetramethoxynaphthalene-2-yl)-ethanol
  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：

  ((3aR,5R,6S,6aR)-2,2-Dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-methyl-carbamic acid methyl ester 在 重铬酸吡啶 、 正丁基锂 、 碘 、 乙酸酐 、 碳酸氢钠 、 对甲苯磺酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 40.0h， 生成 {(4R)-[(1R)-hydroxy-1-(1,4,5,8-tetramethoxynaphthalene-2-yl)-ethyl]-(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