ammonium (methyl 5-amino-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosid)onate | 1454817-58-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ammonium (methyl 5-amino-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosid)onate
• 英文别名: (2S,4S,5R,6R)-5-amino-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid;azane
• CAS: 1454817-58-3
• 化学式: C₁₀H₁₉NO₈*H₃N
• 分子量: 298.293
• InChiKey: PIDHITRAMMSROR-KOLMDWNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.23
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  164
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ammonium (methyl 5-amino-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosid)onate 、 乙酰氧基乙酰氯 在 三乙胺 、 甲醇 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以91%的产率得到methyl 3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-β-D-galacto-non-2-ulopyranosidonic acid
  参考文献：
  名称：

  Microwave-assisted synthesis of N-glycolylneuraminic acid derivatives

  摘要：

  A rapid, efficient and scalable synthesis of biologically-relevant N-glycolylneuraminic acid derivatives from the natural N-acetyl (Neu5Ac) precursors has been developed. Microwave irradiation provides accelerated de-N-acetylation compared to more traditional methods, with optimised NaOH-promoted de-N-acetylation in only 15 min. The prepared amines were readily re-N-acylated to afford the corresponding N-glycolyl (Neu5Gc) analogues. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.107
• 作为产物：
  描述：

  methyl (methyl 5-acetamido-3,5-dideoxy-D-glycero-β-Dgalacto-non-2-ulopyranosid)onate 在 sodium hydroxide 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 0.25h， 以82%的产率得到ammonium (methyl 5-amino-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosid)onate
  参考文献：
  名称：

  Microwave-assisted synthesis of N-glycolylneuraminic acid derivatives

  摘要：

  A rapid, efficient and scalable synthesis of biologically-relevant N-glycolylneuraminic acid derivatives from the natural N-acetyl (Neu5Ac) precursors has been developed. Microwave irradiation provides accelerated de-N-acetylation compared to more traditional methods, with optimised NaOH-promoted de-N-acetylation in only 15 min. The prepared amines were readily re-N-acylated to afford the corresponding N-glycolyl (Neu5Gc) analogues. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.107

文献信息

• Microwave-assisted synthesis of N-glycolylneuraminic acid derivatives
  作者：Pradeep Chopra、Paul D. Madge、Robin J. Thomson、I. Darren Grice、Mark von Itzstein

  DOI：10.1016/j.tetlet.2013.07.107

  日期：2013.10

  A rapid, efficient and scalable synthesis of biologically-relevant N-glycolylneuraminic acid derivatives from the natural N-acetyl (Neu5Ac) precursors has been developed. Microwave irradiation provides accelerated de-N-acetylation compared to more traditional methods, with optimised NaOH-promoted de-N-acetylation in only 15 min. The prepared amines were readily re-N-acylated to afford the corresponding N-glycolyl (Neu5Gc) analogues. (C) 2013 Elsevier Ltd. All rights reserved.