N-allyloxycarbonyl 1-amino-2,4-diacetamido-2,4,6-trideoxy-β-D-glucopyranose | 904891-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-allyloxycarbonyl 1-amino-2,4-diacetamido-2,4,6-trideoxy-β-D-glucopyranose
• CAS: 904891-36-7
• 化学式: C₁₄H₂₃N₃O₆
• 分子量: 329.353
• InChiKey: ORAWPXOGBRZBQT-KDRYVUTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.99
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  125.99
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-allyloxycarbonyl 1-amino-2,4-diacetamido-2,4,6-trideoxy-β-D-glucopyranose 、 Fmoc-Asp(F)-O-t-Bu 在 四(三苯基膦)钯 、 苯硅烷 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 21.0h， 以86%的产率得到N^α-fluoren-9-ylmethyloxycarbonyl-N^t-(2,4-diacetamido-2,4,6-trideoxy-β-D-glucopyranosyl)-L-aspargine t-butyl ester
  参考文献：
  名称：

  Synthesis of asparagine-linked bacillosamine

  摘要：

  Various types of protein glycosylation have been identified from prokaryotes. Recent investigations have revealed the presence of N-linked glycoproteins in the pathogenic bacterium, Campylobacter jejuni. The structure of this glycan is unique, consisting of 5 Ga1NAc and 1 G1c, in addition to 2,4-diacetamido-2,4,6-trideoxy-D-glucopyranose (bacillosamine; Bac), which is N-glycosidically linked to the side chain of asparagine (Asn). We synthesized Bac from a 2-azido-2-deoxy-D-galactose derivative, which was further converted to the Asn-linked form. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2006.04.031
• 作为产物：
  描述：

  2,4-diacetamido-2,4,6-trideoxy-D-glucopyranose 在 碳酸氢钠 、 碳酸氢铵 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 77.5h， 生成 N-allyloxycarbonyl 1-amino-2,4-diacetamido-2,4,6-trideoxy-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of asparagine-linked bacillosamine

  摘要：

  Various types of protein glycosylation have been identified from prokaryotes. Recent investigations have revealed the presence of N-linked glycoproteins in the pathogenic bacterium, Campylobacter jejuni. The structure of this glycan is unique, consisting of 5 Ga1NAc and 1 G1c, in addition to 2,4-diacetamido-2,4,6-trideoxy-D-glucopyranose (bacillosamine; Bac), which is N-glycosidically linked to the side chain of asparagine (Asn). We synthesized Bac from a 2-azido-2-deoxy-D-galactose derivative, which was further converted to the Asn-linked form. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2006.04.031