Acetic acid (1S,2R,3S)-2,3,4-triacetoxy-1-{(S)-acetoxy-[2-(3,4-dimethoxy-phenyl)-ethylcarbamoyl]-methyl}-butyl ester | 182892-18-8

• 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: Acetic acid (1S,2R,3S)-2,3,4-triacetoxy-1-{(S)-acetoxy-[2-(3,4-dimethoxy-phenyl)-ethylcarbamoyl]-methyl}-butyl ester
• CAS: 182892-18-8
• 化学式: C₂₆H₃₅NO₁₃
• 分子量: 569.563
• InChiKey: AEFULORMLABPCO-NDBXHCKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  40.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  179.06
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2R,3S)-2,3,4-triacetoxy-1-{(S)-acetoxy-[2-(3,4-dimethoxy-phenyl)-ethylcarbamoyl]-methyl}-butyl ester 在 五氯化磷 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 Acetic acid (1R,2R,3R,4S)-2,3,4,5-tetraacetoxy-1-(6,7-dimethoxy-2-oxy-3,4-dihydro-isoquinolin-1-yl)-pentyl ester
  参考文献：
  名称：

  Enantioselective synthesis of (R)-(−)-laudanosine and (R)-(−)-glaucine from L-ascorbic acid

  摘要：

  L-Ascorbic acid 1 was converted into L-gulonolactone 2 by catalytic hydrogenation. Treatment of 2 with 3,4-dimethoxyphenylethyl amine 3 afforded amide 4, which in several steps was transformed into the title alkaloids in good enantiomeric excesses. Also, chromium(III) oxide is proposed as an effective catalyst for the conversion of (R)-(-)-laudanosine into (R)-(-)-glaucine. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00349-7
• 作为产物：
  描述：

  乙酸酐 、 (2S,3S,4R,5S)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2,3,4,5,6-pentahydroxyhexanamide 在 吡啶 作用下， 反应 72.0h， 以83%的产率得到Acetic acid (1S,2R,3S)-2,3,4-triacetoxy-1-{(S)-acetoxy-[2-(3,4-dimethoxy-phenyl)-ethylcarbamoyl]-methyl}-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of (R)-(−)-laudanosine and (R)-(−)-glaucine from L-ascorbic acid

  摘要：

  L-Ascorbic acid 1 was converted into L-gulonolactone 2 by catalytic hydrogenation. Treatment of 2 with 3,4-dimethoxyphenylethyl amine 3 afforded amide 4, which in several steps was transformed into the title alkaloids in good enantiomeric excesses. Also, chromium(III) oxide is proposed as an effective catalyst for the conversion of (R)-(-)-laudanosine into (R)-(-)-glaucine. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00349-7