((3aR,5R,6S,6aR)-2,2-Dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-methyl-carbamic acid methyl ester | 205868-30-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3aR,5R,6S,6aR)-2,2-Dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-methyl-carbamic acid methyl ester
• 英文别名: methyl N-[(3aR,5R,6S,6aR)-5-ethenyl-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]-N-methylcarbamate
• CAS: 205868-30-0
• 化学式: C₁₂H₁₉NO₅
• 分子量: 257.287
• InChiKey: FYCCPQFUYBZKSK-UTINFBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 碘 、 碳酸氢钠 、 对甲苯磺酸 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 32.0h， 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
• 作为产物：
  描述：

  3-deoxy-3-(N-methoxycarbonyl-N-methylamino)-1,2-O-isopropylidene-α-D-glucofuranose 在 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 丁酮 为溶剂， 反应 15.0h， 生成 ((3aR,5R,6S,6aR)-2,2-Dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-methyl-carbamic 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