tert-butyl (1S)-6,8-bis(phenylmethoxy)-1-[(3R)-4,4,4-trichloro-3-hydroxybutyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate | 1127644-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: tert-butyl (1S)-6,8-bis(phenylmethoxy)-1-[(3R)-4,4,4-trichloro-3-hydroxybutyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 1127644-99-8
• 化学式: C₃₂H₃₆Cl₃NO₅
• 分子量: 621.001
• InChiKey: DGMXMXBHUDLZHU-XTEPFMGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S)-6,8-bis(phenylmethoxy)-1-[(3R)-4,4,4-trichloro-3-hydroxybutyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate 在 sodium hydroxide 、 sodium azide 、 水 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 生成 (2S)-2-azido-4-[(1S)-2-[(2-methylpropan-2-yl)oxycarbonyl]-6,8-bis(phenylmethoxy)-3,4-dihydro-1H-isoquinolin-1-yl]butanoic acid
  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
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (2R)-4-[(1S)-6,8-bis(phenylmethoxy)-1,2,3,4-tetrahydroisoquinolin-1-yl]-1,1,1-trichlorobutan-2-ol 以 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到tert-butyl (1S)-6,8-bis(phenylmethoxy)-1-[(3R)-4,4,4-trichloro-3-hydroxybutyl]-3,4-dihydro-1H-isoquinoline-2-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.