12-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-1,15-pentadecanlactam | 1018688-38-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 12-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-1,15-pentadecanlactam
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(5S)-16-oxo-azacyclohexadec-5-yl]oxy]oxan-2-yl]methyl benzoate
• CAS: 1018688-38-4
• 化学式: C₄₉H₅₅NO₁₁
• 分子量: 833.976
• InChiKey: WMCCIUGSOPTCPG-VQVOKWHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  61
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  12-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-1,15-pentadecanlactam 在 氨 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以76%的产率得到(S)-12-hydroxy-1,15-pentadecanlactam
  参考文献：
  名称：

  Resolution of racemic 12-hydroxyl-1,15-pentadecanlactam using d-glucose derivative as a chiral auxiliary

  摘要：

  Racemic 12-hydroxyl-1,15-pentadecanlactam 2 was resolved using glucose as a chiral auxiliary for the first time. Both the (R)- and (S)-isomers were obtained in high enantiomeric excesses (>99% by HPLC). The absolute configuration of (+)-2b and (-)-2a was determined by Horeau's method and a modified Mosher's method. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.007
• 作为产物：
  描述：

  12-hydroxy-1,15-pentadecanlactam 、 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以1.8 g的产率得到12-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-1,15-pentadecanlactam
  参考文献：
  名称：

  Resolution of racemic 12-hydroxyl-1,15-pentadecanlactam using d-glucose derivative as a chiral auxiliary

  摘要：

  Racemic 12-hydroxyl-1,15-pentadecanlactam 2 was resolved using glucose as a chiral auxiliary for the first time. Both the (R)- and (S)-isomers were obtained in high enantiomeric excesses (>99% by HPLC). The absolute configuration of (+)-2b and (-)-2a was determined by Horeau's method and a modified Mosher's method. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.007

文献信息

• Resolution of racemic 12-hydroxyl-1,15-pentadecanlactam using d-glucose derivative as a chiral auxiliary
  作者：Chuan-Jin Hou、Xiao-Mei Liang、Jing-Ping Wu、Jia-Xing Huang、Jian-Jun Zhang、Dao-Quan Wang

  DOI：10.1016/j.tetasy.2008.01.007

  日期：2008.2

  Racemic 12-hydroxyl-1,15-pentadecanlactam 2 was resolved using glucose as a chiral auxiliary for the first time. Both the (R)- and (S)-isomers were obtained in high enantiomeric excesses (>99% by HPLC). The absolute configuration of (+)-2b and (-)-2a was determined by Horeau's method and a modified Mosher's method. (C) 2008 Elsevier Ltd. All rights reserved.