(4S,5R)-4-benzyloxy-5-hydroxy-N-(4-methoxybenzyl)heptanoyl amide | 1160427-18-8

• 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: (4S,5R)-4-benzyloxy-5-hydroxy-N-(4-methoxybenzyl)heptanoyl amide
• CAS: 1160427-18-8
• 化学式: C₂₂H₂₉NO₄
• 分子量: 371.477
• InChiKey: DJKQDUNYQFZTGS-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  27.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-benzyloxy-5-hydroxy-N-(4-methoxybenzyl)heptanoyl amide 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Chemo- and diastereoselective control for a flexible approach to (5S,6S)-6-alkyl-5-benzyloxy-2-piperidinones

  摘要：

  Chemo- and diastereoselective transformation of the N,O-acetals and their chain tautomers (4/5), readily derived from protected 3-hydroxyglutamide 1a, Was Studied. It Was Uncovered that while the reaction with a combination of boron trifluoride etherate/zinc borohydride led to cyclic products (5S,6S/R)-6-alkyl-5-benzyloxy-2-piperidinones 3/2, and 6 in modest chemo- and diastereoselectivities, the reaction of 4/5 with zinc borohydride led exclusively to the formation of the ring-opening products 6 in excellent anti-diastereoselectivities. On the basis of the latter reaction, a flexible approach to (5S,6S)-6-alkyl-5-benzyloxy-2-piperidinones 3 was disclosed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.021
• 作为产物：
  描述：

  (5S)-6-ethyl-6-hydroxy-1-[(4-methoxyphenyl)methyl]-5-phenylmethoxypiperidin-2-one 在 zinc(II) tetrahydroborate 作用下， 以 乙醚 为溶剂， 生成 (4S,5R)-4-benzyloxy-5-hydroxy-N-(4-methoxybenzyl)heptanoyl amide 、 4-benzyloxy-5-hydroxy-N-(4-methoxybenzyl)heptanoyl amide
  参考文献：
  名称：

  Chemo- and diastereoselective control for a flexible approach to (5S,6S)-6-alkyl-5-benzyloxy-2-piperidinones

  摘要：

  Chemo- and diastereoselective transformation of the N,O-acetals and their chain tautomers (4/5), readily derived from protected 3-hydroxyglutamide 1a, Was Studied. It Was Uncovered that while the reaction with a combination of boron trifluoride etherate/zinc borohydride led to cyclic products (5S,6S/R)-6-alkyl-5-benzyloxy-2-piperidinones 3/2, and 6 in modest chemo- and diastereoselectivities, the reaction of 4/5 with zinc borohydride led exclusively to the formation of the ring-opening products 6 in excellent anti-diastereoselectivities. On the basis of the latter reaction, a flexible approach to (5S,6S)-6-alkyl-5-benzyloxy-2-piperidinones 3 was disclosed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.021

文献信息

• A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S,5S)-Dihydroxy Amides
  作者：Bo Yin、Dong-Nai Ye、Kai-Hui Yu、Liang-Xian Liu

  DOI：10.3390/molecules15042771

  日期：——

  A general approach to (4S,5S)-4-benzyloxy-5-hydroxy-N-(4-methoxybenzyl) amides 10 based on a diastereoselective reduction of (5S,6RS)-6-alkyl-5-benzyloxy-6-hydroxy-2-piperidinones 6 and their tautomeric ring-opened keto amides 7 is described. The reduction with L-Selectride at -20 °C to room temperature afforded the products 10 in excellent yields and moderate to high syn-diastereoselectivities.

  本文介绍了一种基于非对映选择性还原 (5S,6RS)-6-烷基-5-苄氧基-6-羟基-2-哌啶酮 6 及其同分异构体开环酮酰胺 7 的 (4S,5S)-4-苄氧基-5-羟基-N-(4-甲氧基苄基)酰胺 10 的一般方法。在 -20 °C 至室温条件下，用 L-选择性氮化物进行还原，得到了产率极佳、具有中等至高同-非对映选择性的产物 10。