[(1R,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-((R)-toluene-4-sulfinyl)-propyl]-carbamic acid benzyl ester | 737767-62-3

• 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: [(1R,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-((R)-toluene-4-sulfinyl)-propyl]-carbamic acid benzyl ester
• CAS: 737767-62-3
• 化学式: C₃₉H₅₁N₃O₄S
• 分子量: 657.918
• InChiKey: HSEMDOLENBRSMI-HUDXANGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  87.74
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(1R,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-((R)-toluene-4-sulfinyl)-propyl]-carbamic acid benzyl ester 在 2,4,6-三甲基吡啶 、 氢氧化钾 、 三氟乙酸酐 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 (-)-(3S,4aS,8aS,2'R,3'R)-2-[3'-amino-2'-hydroxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide
  参考文献：
  名称：

  Stereocontrolled synthesis of hydroxyethylamine isosteres via chiral sulfoxide chemistry

  摘要：

  A novel synthesis of enantiopure hydroxyethylamine isosteres has been developed. Reaction of lithiated beta-sulfinyl-ethylamines 3 with N-Cbz-irnines generated in situ from alpha-amino-sulfones 4 afforded in good to excellent yields and moderate stereocontrol the 2-sulfinyl-1,3-diamines 2. The latter were submitted to the nonoxidative Pummerer reaction (NOPR) in CH2Cl2, that produced the target compounds 1 in very good yields with inversion Of Configuration. In some cases, the use of acetonitrile as solvent resulted in a double-inversion pathway, leading for example to the oxazolidinone 5. The total synthesis of an epimer of Saquinavir has been achieved by this method. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.160
• 作为产物：
  描述：

  (R)-p-tolyl vinyl sulfoxide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 60.0h， 生成 [(1R,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-((R)-toluene-4-sulfinyl)-propyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Stereocontrolled synthesis of hydroxyethylamine isosteres via chiral sulfoxide chemistry

  摘要：

  A novel synthesis of enantiopure hydroxyethylamine isosteres has been developed. Reaction of lithiated beta-sulfinyl-ethylamines 3 with N-Cbz-irnines generated in situ from alpha-amino-sulfones 4 afforded in good to excellent yields and moderate stereocontrol the 2-sulfinyl-1,3-diamines 2. The latter were submitted to the nonoxidative Pummerer reaction (NOPR) in CH2Cl2, that produced the target compounds 1 in very good yields with inversion Of Configuration. In some cases, the use of acetonitrile as solvent resulted in a double-inversion pathway, leading for example to the oxazolidinone 5. The total synthesis of an epimer of Saquinavir has been achieved by this method. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.160