(1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde | 853786-26-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde
• 英文别名: 3-[(S)-[3,5-dimethoxy-4-(methoxymethoxy)phenyl]-[(2R)-oxiran-2-yl]methoxy]-4-phenylmethoxybenzaldehyde
• CAS: 853786-26-2
• 化学式: C₂₇H₂₈O₈
• 分子量: 480.515
• InChiKey: MLRNYRPVJREHPV-FTJBHMTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 9.0h， 以71%的产率得到(1'S,2'R)-4-hydroxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde
  参考文献：
  名称：

  An enantioselective total synthesis of the stilbenolignan (−)-aiphanol and the determination of its absolute stereochemistry

  摘要：

  The title natural product (-)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3,5-dimethoxy-4-(methoxymethoxy)cinnamyl alcohol with the AD-mix-beta to give triol (1R,2R)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These Studies have established that the naturally occurring enantiomer of aiphanol possesses the (S)-configuration at each of C-2' and C-3'. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.035
• 作为产物：
  描述：

  3,5-dimethoxy-4-(methoxymethoxy)benzaldehyde 在 吡啶 、 甲基磺酰胺 、 偶氮二甲酸二异丙酯 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 79.0h， 生成 (1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde
  参考文献：
  名称：

  An enantioselective total synthesis of the stilbenolignan (−)-aiphanol and the determination of its absolute stereochemistry

  摘要：

  The title natural product (-)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3,5-dimethoxy-4-(methoxymethoxy)cinnamyl alcohol with the AD-mix-beta to give triol (1R,2R)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These Studies have established that the naturally occurring enantiomer of aiphanol possesses the (S)-configuration at each of C-2' and C-3'. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.035

文献信息

• An enantioselective total synthesis of the stilbenolignan (−)-aiphanol and the determination of its absolute stereochemistry
  作者：Martin G. Banwell、Satish Chand、G. Paul Savage

  DOI：10.1016/j.tetasy.2005.02.035

  日期：2005.5

  The title natural product (-)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3,5-dimethoxy-4-(methoxymethoxy)cinnamyl alcohol with the AD-mix-beta to give triol (1R,2R)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These Studies have established that the naturally occurring enantiomer of aiphanol possesses the (S)-configuration at each of C-2' and C-3'. (C) 2005 Elsevier Ltd. All rights reserved.