ammonium (methyl 5-amino-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate | 1454818-67-7

• 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-α-D-galacto-non-2-ulopyranosid)onate
• CAS: 1454818-67-7
• 化学式: C₁₀H₁₉NO₈*H₃N
• 分子量: 298.293
• InChiKey: PIDHITRAMMSROR-VANPNGPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.23
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  197.7
• 氢给体数：
  7.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ammonium (methyl 5-amino-3,5-dideoxy-D-glycero-α-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85%的产率得到methyl 3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-α-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 4,7,8,9-tetra-O-acetyl-5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranoside]onate 在 sodium hydroxide 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 0.25h， 以80%的产率得到ammonium (methyl 5-amino-3,5-dideoxy-D-glycero-α-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