2-acetamido-1,3-di-O-acetyl-2-deoxy-α-D-mannose | 74950-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-1,3-di-O-acetyl-2-deoxy-α-D-mannose
• 英文别名: [(2R,3S,4R,5S,6R)-3-acetamido-2-acetyloxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl] acetate
• CAS: 74950-69-9
• 化学式: C₁₂H₁₉NO₈
• 分子量: 305.285
• InChiKey: SAKVPCXJVMFXTF-ROHXPCBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-acetamido-1,3-di-O-acetyl-2-deoxy-α-D-mannose 在 吡啶 、 platinum(IV) oxide 、 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 120.0h， 生成 2-acetamido-2-deoxy-D-mannose 6-phosphate
  参考文献：
  名称：

  Comparison of chemical and enzymatic synthesis of 2-acetamido-2-deoxy-d-mannose 6-phosphate: a new approach

  摘要：

  Chemical and enzymatic methods to synthesis of 2-acetamido-2-deoxy-D-mannose-6-phosphate (ManNAc-6-P) have been investigated. A new preparative method has been developed although some established procedures were tried. In this new method, a 6-O-acetyl or 4,6-di-O-acetyl group of the per-O-acetylated 2-acetamido-2-deoxy-D-mannose (ManNAc) were regioselectively removed with an esterase from the yellow yeast, Rhonosporidium toruloides, followed by phosphorylation and O-deacetylation under mild conditions. H-1 and C-13 NMR data spectra of ManNAc-6-P were recorded. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00299-8
• 作为产物：
  描述：

  2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-mannopyranose 在 Rhodosporidium toruloides 作用下， 以 水 为溶剂， 反应 30.0h， 以46%的产率得到1,3,4-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Comparison of chemical and enzymatic synthesis of 2-acetamido-2-deoxy-d-mannose 6-phosphate: a new approach

  摘要：

  Chemical and enzymatic methods to synthesis of 2-acetamido-2-deoxy-D-mannose-6-phosphate (ManNAc-6-P) have been investigated. A new preparative method has been developed although some established procedures were tried. In this new method, a 6-O-acetyl or 4,6-di-O-acetyl group of the per-O-acetylated 2-acetamido-2-deoxy-D-mannose (ManNAc) were regioselectively removed with an esterase from the yellow yeast, Rhonosporidium toruloides, followed by phosphorylation and O-deacetylation under mild conditions. H-1 and C-13 NMR data spectra of ManNAc-6-P were recorded. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00299-8