methyl (S)-4-hydroxy-5-(4-methoxybenzylamino)-5-oxopentanoate | 908040-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl (S)-4-hydroxy-5-(4-methoxybenzylamino)-5-oxopentanoate
• CAS: 908040-18-6
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: PGAUEJSVOCRABV-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (S)-4-hydroxy-5-(4-methoxybenzylamino)-5-oxopentanoate 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 、 calcium chloride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 (S)-4-(tret-butyldimethylsilyloxy)-5-(4-methoxybenzylamino)-5-oxopentyl methanesulfonate
  参考文献：
  名称：

  Syntheses of enantio-enriched chiral building blocks from l-glutamic acid

  摘要：

  Starting from lactone-amide 8, easily derived from L-glutamic acid, enantioselective syntheses of (S)-tetrahydrofuran 2-carboxamide derivative 2 and a protected (S)-3-hydroxypiperidin-2-one (3) are reported. The building block 3 was converted to (2S,3R)-3-hydroxypipecolamide (6) by a three-step procedure. A solvent altered H-bonding capacity leading to a highly chemoselective tosylation of the primary hydroxyl group in the presence of an alpha-hydroxy-carboxamide was observed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.013
• 作为产物：
  描述：

  甲醇 、 (S)-N-(4-甲氧基苄基)-四氢-5-氧代-2-呋喃甲酰胺 在 硫酸 作用下， 反应 1.5h， 以93%的产率得到methyl (S)-4-hydroxy-5-(4-methoxybenzylamino)-5-oxopentanoate
  参考文献：
  名称：

  Syntheses of enantio-enriched chiral building blocks from l-glutamic acid

  摘要：

  Starting from lactone-amide 8, easily derived from L-glutamic acid, enantioselective syntheses of (S)-tetrahydrofuran 2-carboxamide derivative 2 and a protected (S)-3-hydroxypiperidin-2-one (3) are reported. The building block 3 was converted to (2S,3R)-3-hydroxypipecolamide (6) by a three-step procedure. A solvent altered H-bonding capacity leading to a highly chemoselective tosylation of the primary hydroxyl group in the presence of an alpha-hydroxy-carboxamide was observed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.013