2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranose | 172950-49-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranose
• 英文别名: [(2R,3S,4R,5S,6R)-5-acetamido-3,6-diacetyloxy-4-hydroxyoxan-2-yl]methyl acetate
• CAS: 172950-49-1
• 化学式: C₁₄H₂₁NO₉
• 分子量: 347.322
• InChiKey: PFVVPVIQHUPVQO-ITGHMWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranose 在 吡啶 作用下， 以94.9%的产率得到2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-3-O-methylsulfonyl-α-D-mannopyranose
  参考文献：
  名称：

  Versatile intermediates in the selective modification of the amino function of 2-amino-2-deoxy-d-mannopyranose and the 3-position of 2-acetamido-2-deoxy-d-mannose: Potential membrane modifiers in neoplastic control

  摘要：

  A general method has been developed to selectively modify the amino group of 2-amino-2-deoxy-D-mannopyranose (D-mannosamine), a precursor of the terminal membrane sugar, sialic acid. 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-alpha-D-mannopyranose oxalate was prepared via two routes that allowed introduction of various acyl groups onto the amino function. These compounds were evaluated for their antineoplastic properties. The most significant preclinical therapeutic finding was the antileukemic activity found in mice for tetra-O-acetyl-2-epi-streptozotocin (the acetylated alpha-mannosamine epimer of streptozotocin). Administration of 50 mg/kg/day X 5 to leukemia L1210-bearing DBA/2Ha mice resulted in 5/5 35-day survivors. Neutralization of 1,3,3,6-tetra-O-acetyl-2-amino-2-deoxy-alpha-D-mannopyranose oxalate under aqueous conditions led to 2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-alpha-D-mannopyranose, the oxidation of which gave 2-acetamido-4,6-di-O-acetyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose. This agent demonstrated an IC50 of 25 mu M with a murine L1210 cell culture. Administration of 100 mg/kg/day X 5 resulted in 42% ILS in DBA/2 mice with ip L1210 leukemia. Several other nonacetylated derivatives were also prepared by direct N-acylation, producing, for example, fluorescently tagged N-dansylmannosamine.

  DOI：

  10.1016/0008-6215(95)00154-l
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-α-D-mannopyranoseoxalate salt 在 sodium acetate 作用下， 以 水 为溶剂， 以30%的产率得到2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranose
  参考文献：
  名称：

  Versatile intermediates in the selective modification of the amino function of 2-amino-2-deoxy-d-mannopyranose and the 3-position of 2-acetamido-2-deoxy-d-mannose: Potential membrane modifiers in neoplastic control

  摘要：

  A general method has been developed to selectively modify the amino group of 2-amino-2-deoxy-D-mannopyranose (D-mannosamine), a precursor of the terminal membrane sugar, sialic acid. 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-alpha-D-mannopyranose oxalate was prepared via two routes that allowed introduction of various acyl groups onto the amino function. These compounds were evaluated for their antineoplastic properties. The most significant preclinical therapeutic finding was the antileukemic activity found in mice for tetra-O-acetyl-2-epi-streptozotocin (the acetylated alpha-mannosamine epimer of streptozotocin). Administration of 50 mg/kg/day X 5 to leukemia L1210-bearing DBA/2Ha mice resulted in 5/5 35-day survivors. Neutralization of 1,3,3,6-tetra-O-acetyl-2-amino-2-deoxy-alpha-D-mannopyranose oxalate under aqueous conditions led to 2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-alpha-D-mannopyranose, the oxidation of which gave 2-acetamido-4,6-di-O-acetyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose. This agent demonstrated an IC50 of 25 mu M with a murine L1210 cell culture. Administration of 100 mg/kg/day X 5 resulted in 42% ILS in DBA/2 mice with ip L1210 leukemia. Several other nonacetylated derivatives were also prepared by direct N-acylation, producing, for example, fluorescently tagged N-dansylmannosamine.

  DOI：

  10.1016/0008-6215(95)00154-l