(2,3:4,5-di-O-isopropylidene)galactaric acid methyl ester N-dodecylamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3:4,5-di-O-isopropylidene)galactaric acid methyl ester N-dodecylamide
• 英文别名: methyl (4S,5R)-5-[(4S,5R)-5-(dodecylcarbamoyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• 化学式: C₂₅H₄₅NO₇
• 分子量: 471.635
• InChiKey: OBDYXZATUXKJPH-BQJUDKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2,3:4,5-di-O-isopropylidene)galactaric acid methyl ester N-dodecylamide 在 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 N-[2-({5-[(3aS,4R,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl}amino)ethyl]-N'-dodecyl galactaric acid diamide
  参考文献：
  名称：

  Synthesis of a biotinated amphiphile

  摘要：

  The synthesis of a biotinated amphiphile assembled from D-(+)-biotin, ethylene diamine as spacer, galactaric acid and 1-dodecylamine was achieved in six steps. The key step was the synthesis of a bisacetonide protected galactaric ester, the structure of which was determined by X-ray analysis. Aminolysis, spacer attachment, coupling with biotin and deprotection led to the amphiphilic galactaramide. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.09.063
• 作为产物：
  描述：

  dimethyl galactarate 在 sodium methylate 、 三氯化铁 作用下， 以 甲醇 为溶剂， 反应 23.5h， 生成 (2,3:4,5-di-O-isopropylidene)galactaric acid methyl ester N-dodecylamide
  参考文献：
  名称：

  Synthesis of a biotinated amphiphile

  摘要：

  The synthesis of a biotinated amphiphile assembled from D-(+)-biotin, ethylene diamine as spacer, galactaric acid and 1-dodecylamine was achieved in six steps. The key step was the synthesis of a bisacetonide protected galactaric ester, the structure of which was determined by X-ray analysis. Aminolysis, spacer attachment, coupling with biotin and deprotection led to the amphiphilic galactaramide. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.09.063

文献信息

• Synthesis of a biotinated amphiphile
  作者：Sabine Amslinger、Andreas Hirsch、Frank Hampel

  DOI：10.1016/j.tet.2004.09.063

  日期：2004.12

  The synthesis of a biotinated amphiphile assembled from D-(+)-biotin, ethylene diamine as spacer, galactaric acid and 1-dodecylamine was achieved in six steps. The key step was the synthesis of a bisacetonide protected galactaric ester, the structure of which was determined by X-ray analysis. Aminolysis, spacer attachment, coupling with biotin and deprotection led to the amphiphilic galactaramide. (C) 2004 Published by Elsevier Ltd.