triethyl-[(E,2R)-1,1,1-trichloro-5-methoxypent-4-en-2-yl]oxysilane | 1127645-19-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: triethyl-[(E,2R)-1,1,1-trichloro-5-methoxypent-4-en-2-yl]oxysilane
• CAS: 1127645-19-5
• 化学式: C₁₂H₂₃Cl₃O₂Si
• 分子量: 333.758
• InChiKey: ZNDGLCQWOCOIPQ-RJCSOLBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲氧基甲基三苯基氯化膦 、 (3R)-4,4,4-trichloro-3-triethylsilyloxybutanal 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 triethyl-[(Z,2R)-1,1,1-trichloro-5-methoxypent-4-en-2-yl]oxysilane 、 triethyl-[(E,2R)-1,1,1-trichloro-5-methoxypent-4-en-2-yl]oxysilane
  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.