(1'S,5'R)-3-{[3',3'-dimethyl-5'-(2''-methylpropyl)(2',4'-dioxolanyl)]methyl}-2-formylphenol | 244203-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'S,5'R)-3-{[3',3'-dimethyl-5'-(2''-methylpropyl)(2',4'-dioxolanyl)]methyl}-2-formylphenol
• 英文别名: 2-[[(4S,5R)-2,2-dimethyl-5-(2-methylpropyl)-1,3-dioxolan-4-yl]methyl]-6-hydroxybenzaldehyde
• CAS: 244203-41-6
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: NVFRYNMAYGMHLL-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1'S,5'R)-3-{[3',3'-dimethyl-5'-(2''-methylpropyl)(2',4'-dioxolanyl)]methyl}-2-formylphenol 在 palladium dihydroxide 、 sodium hydrogensulfite 盐酸 、 sodium chlorite 、 sodium dihydrogenphosphate 、 sodium azide 、 高氯酸 、 18-冠醚-6 、 氢气 、 双氧水 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 52.33h， 生成 (1S,3'S)-<1-(3,4-Dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3-methylbutyl> ammonium chloride
  参考文献：
  名称：

  A New Enantioselective Total Synthesis of AI-77-B

  摘要：

  [GRAPHICS]An enantioselective total synthesis of Al-77-B (1), a gastroprotective substance isolated from a culture broth of Bacillus pumilus Al- 77, was performed in high overall yield. In this synthesis, the dihydroisocoumarin part 14 and the dihydroxyamino acid part 20 were both assembled from D-ribose as the common chiral source, For the construction of 14 a bromobenzofuran derivative was used as a novel salicylic acid synthon. Finally, DEPC-mediated condensation of 14 and 20 yielded Al-77-B (1).

  DOI：

  10.1021/ol990102y
• 作为产物：
  描述：

  2,3-异亚丙氧基-D-呋喃核糖苷 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 14.83h， 生成 (1'S,5'R)-3-{[3',3'-dimethyl-5'-(2''-methylpropyl)(2',4'-dioxolanyl)]methyl}-2-formylphenol
  参考文献：
  名称：

  A New Enantioselective Total Synthesis of AI-77-B

  摘要：

  [GRAPHICS]An enantioselective total synthesis of Al-77-B (1), a gastroprotective substance isolated from a culture broth of Bacillus pumilus Al- 77, was performed in high overall yield. In this synthesis, the dihydroisocoumarin part 14 and the dihydroxyamino acid part 20 were both assembled from D-ribose as the common chiral source, For the construction of 14 a bromobenzofuran derivative was used as a novel salicylic acid synthon. Finally, DEPC-mediated condensation of 14 and 20 yielded Al-77-B (1).

  DOI：

  10.1021/ol990102y

文献信息

• A New Enantioselective Total Synthesis of AI-77-B
  作者：Hiyoshizo Kotsuki、Tomohiro Araki、Aya Miyazaki、Mitsuhiro Iwasaki、Probal K. Datta

  DOI：10.1021/ol990102y

  日期：1999.8.1

  [GRAPHICS]An enantioselective total synthesis of Al-77-B (1), a gastroprotective substance isolated from a culture broth of Bacillus pumilus Al- 77, was performed in high overall yield. In this synthesis, the dihydroisocoumarin part 14 and the dihydroxyamino acid part 20 were both assembled from D-ribose as the common chiral source, For the construction of 14 a bromobenzofuran derivative was used as a novel salicylic acid synthon. Finally, DEPC-mediated condensation of 14 and 20 yielded Al-77-B (1).