Toluene-4-sulfonic acid (S)-4-hydroxy-1-(4-methoxy-benzylcarbamoyl)-butyl ester | 908040-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid (S)-4-hydroxy-1-(4-methoxy-benzylcarbamoyl)-butyl ester
• CAS: 908040-14-2
• 化学式: C₂₀H₂₅NO₆S
• 分子量: 407.488
• InChiKey: JXSLKNCQBTZUMH-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (S)-4-hydroxy-1-(4-methoxy-benzylcarbamoyl)-butyl ester 生成 (R)-N-(4-methoxybenzyl)-tetrahydrofuran-2-carboxamide
  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：

  (S)-N-(4-甲氧基苄基)-四氢-5-氧代-2-呋喃甲酰胺 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 Toluene-4-sulfonic acid (S)-4-hydroxy-1-(4-methoxy-benzylcarbamoyl)-butyl ester
  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