ammonium 5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate | 1454818-68-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ammonium 5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate
• CAS: 1454818-68-8
• 化学式: C₉H₁₅NO₇*H₃N
• 分子量: 266.251
• InChiKey: HFINXTIXPSPZIN-AFJOUCPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.08
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  188.47
• 氢给体数：
  7.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ammonium 5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate 、 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80%的产率得到(4S,5R,6R)-4-羟基-5-[(2-羟基乙酰基)氨基]-6-[(1R,2R)-1,2,3-三羟基丙基]-5,6-二氢-4H-吡喃-2-羧酸
  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-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 在 sodium hydroxide 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 0.25h， 以85%的产率得到ammonium 5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate
  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