2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucosyl dicyclohexylammonium phosphate | 137845-71-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucosyl dicyclohexylammonium phosphate
• CAS: 137845-71-7
• 化学式: 2C₆H₁₃N*C₁₄H₂₂NO₁₂P
• 分子量: 625.654
• InChiKey: VXZWZSIOVFBVOI-XAWYEFCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  210.01
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucosyl dicyclohexylammonium phosphate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以2.62 g的产率得到2-acetamido-2-deoxy-α-D-glucopyranosyl phosphate mono-cyclohexylammonium salt
  参考文献：
  名称：

  Gram-scale synthesis of uridine 5'-diphospho-N-acetylglucosamine: comparison of enzymic and chemical routes

  摘要：

  Practical chemoenzymatic and chemical routes to uridine 5'-diphospho-N-acetylglucosamine (UDP-GlcNAc) on a gram scale have been developed. The chemoenzymatic synthesis provided convenient access to glucosamine-6-phosphate and N-acetylglucosamine-6-phosphate (GlcNAc-6-P) in > 10-mmol quantities. The condensation between GlcNAc-6-P and UTP was catalyzed by readily available crude enzyme extracts from dried cells of the yeast Candida utilis and afforded a 17% yield of UDP-GlcNAc from GlcNAc-6-P. The otherwise straightforward chemoenzymatic sequence was hampered by the need to purify the product from the final complex reaction mixture. The chemical synthesis of UDP-GlcNAc proceeded through five steps in an overall yield of 15% from penta-acetylglucosamine with the selective formation of tetraacetylglucosamine-alpha-1-phosphate as the key reaction.

  DOI：

  10.1021/jo00027a028
• 作为产物：
  描述：

  (3aR)-2-甲基-5alpha-(乙酰氧基甲基)-6beta,7alpha-二乙酰氧基-3Aalpha,6,7,7Aalpha-四氢-5H-吡喃并[3,2-d]恶唑 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 24.25h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucosyl dicyclohexylammonium phosphate
  参考文献：
  名称：

  Gram-scale synthesis of uridine 5'-diphospho-N-acetylglucosamine: comparison of enzymic and chemical routes

  摘要：

  Practical chemoenzymatic and chemical routes to uridine 5'-diphospho-N-acetylglucosamine (UDP-GlcNAc) on a gram scale have been developed. The chemoenzymatic synthesis provided convenient access to glucosamine-6-phosphate and N-acetylglucosamine-6-phosphate (GlcNAc-6-P) in > 10-mmol quantities. The condensation between GlcNAc-6-P and UTP was catalyzed by readily available crude enzyme extracts from dried cells of the yeast Candida utilis and afforded a 17% yield of UDP-GlcNAc from GlcNAc-6-P. The otherwise straightforward chemoenzymatic sequence was hampered by the need to purify the product from the final complex reaction mixture. The chemical synthesis of UDP-GlcNAc proceeded through five steps in an overall yield of 15% from penta-acetylglucosamine with the selective formation of tetraacetylglucosamine-alpha-1-phosphate as the key reaction.

  DOI：

  10.1021/jo00027a028