methyl (3S,10bS)-8,10-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate | 1127645-08-2

• 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: methyl (3S,10bS)-8,10-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate
• CAS: 1127645-08-2
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: PYLARLRNOHPRFQ-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲醇 、 (R)-1,1,1-trichloro-4-((S)-6,8-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)butan-2-ol 在 sodium azide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 10.0h， 以58%的产率得到methyl (3S,10bS)-8,10-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of Schulzeines B and C via a β-Lactone-Derived Surrogate for Bishomoserine Aldehyde

  摘要：

  Enantioselective syntheses of the glucosidase inhibitors schulzeines B and C were achieved by employing a Pictet-Spengler reaction of a beta-lactone-derived masked bishomoserine aldehyde. Subsequent Corey-Link reaction unveiled an alpha-azido acid enabling cyclization to the delta-lactam fused tetrahydroisoquinoline. An efficient synthesis of the trisulfate-bearing side chain featured a Noyori hydrogenation and a Sharpless dihydroxylation. An unexpected reaction of a pendant amine during a Corey-Link process opens avenues for the synthesis of proline and related amino acid derivatives.

  DOI：

  10.1021/ol802992m

文献信息

• Enantioselective Synthesis of Schulzeines B and C via a β-Lactone-Derived Surrogate for Bishomoserine Aldehyde
  作者：Gang Liu、Daniel Romo

  DOI：10.1021/ol802992m

  日期：2009.3.5

  Enantioselective syntheses of the glucosidase inhibitors schulzeines B and C were achieved by employing a Pictet-Spengler reaction of a beta-lactone-derived masked bishomoserine aldehyde. Subsequent Corey-Link reaction unveiled an alpha-azido acid enabling cyclization to the delta-lactam fused tetrahydroisoquinoline. An efficient synthesis of the trisulfate-bearing side chain featured a Noyori hydrogenation and a Sharpless dihydroxylation. An unexpected reaction of a pendant amine during a Corey-Link process opens avenues for the synthesis of proline and related amino acid derivatives.