(4S,5R)-4-acetamido-5-(2-methylpropyl)tetrahydro-2-furanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4S,5R)-4-acetamido-5-(2-methylpropyl)tetrahydro-2-furanone
• 英文别名: N-[(2R,3S)-2-(2-methylpropyl)-5-oxooxolan-3-yl]acetamide
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: GHOMAGGWVDPJJG-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-2-hydroxy-4-methylpentanenitrile 在 吡啶 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 硫酸 、 sodium methylate 、 臭氧 、 magnesium 作用下， 以 吡啶 、 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 31.25h， 生成 (4S,5R)-4-acetamido-5-(2-methylpropyl)tetrahydro-2-furanone
  参考文献：
  名称：

  Stereoselective synthesis of β-amino-γ-butyrolactones

  摘要：

  A novel synthesis of optically active beta-amino-gamma-butyrolactones is described. O-Silylated (R)-cyanohydrins (R)-3 (derived from aldehydes 1 by (R)-hydroxynitrile lyase ((R)-PaHNL)-catalyzed addition of HCN) were reacted with allyl Grignard to give amino alcohols (4R,5S)-5 after reduction. In the addition of crotyl Grignard reagent, workup conditions are decisive for the formation of amino alcohol 8, which was isolated Lis a diastercoisomeric mixture the acetylated main diastereoisomer (3S,4R,5R)-10 was separated. Ozonolysis of the acetylated amino alcohols (4S,5R)-7a,b and (3S,4S,5R)-10 affords the aldehydes 12a-c, which were directly oxidized with CrO3 in dilute H2SO4 to yield the beta-acetamido-gamma-acetoxycarboxylic acids (3S,4R)-13a,b and (2R,3S,4R)-13c. Compounds 13 cyclized spontaneously Under acidic conditions to afford beta-acetamido-gamma-butyrolactones (4S,5R)-14a,b and (3R,4S,5R)-14c. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00437-8

文献信息

• Stereoselective synthesis of β-amino-γ-butyrolactones
  作者：Jürgen Roos、Franz Effenberger

  DOI：10.1016/s0957-4166(02)00437-8

  日期：2002.9

  A novel synthesis of optically active beta-amino-gamma-butyrolactones is described. O-Silylated (R)-cyanohydrins (R)-3 (derived from aldehydes 1 by (R)-hydroxynitrile lyase ((R)-PaHNL)-catalyzed addition of HCN) were reacted with allyl Grignard to give amino alcohols (4R,5S)-5 after reduction. In the addition of crotyl Grignard reagent, workup conditions are decisive for the formation of amino alcohol 8, which was isolated Lis a diastercoisomeric mixture the acetylated main diastereoisomer (3S,4R,5R)-10 was separated. Ozonolysis of the acetylated amino alcohols (4S,5R)-7a,b and (3S,4S,5R)-10 affords the aldehydes 12a-c, which were directly oxidized with CrO3 in dilute H2SO4 to yield the beta-acetamido-gamma-acetoxycarboxylic acids (3S,4R)-13a,b and (2R,3S,4R)-13c. Compounds 13 cyclized spontaneously Under acidic conditions to afford beta-acetamido-gamma-butyrolactones (4S,5R)-14a,b and (3R,4S,5R)-14c. (C) 2002 Elsevier Science Ltd. All rights reserved.