Methyl-(methyl-5-acetamido-3,4,5-tridesoxy-4-iod-8,9-O-isopropyliden-α-D-manno-2-nonulopyranosid)onat | 110390-90-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-(methyl-5-acetamido-3,4,5-tridesoxy-4-iod-8,9-O-isopropyliden-α-D-manno-2-nonulopyranosid)onat
• 英文别名: methyl (methyl 5-acetamido-3,4,5-trideoxy-4-iodo-8,9-O-isopropylidene-α-D-glycero-2-nonulopyranosid)onate；methyl (2R,4S,5S,6R)-5-acetamido-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-4-iodo-2-methoxyoxane-2-carboxylate
• CAS: 110390-90-4
• 化学式: C₁₆H₂₆INO₈
• 分子量: 487.289
• InChiKey: CMCJNSFYIZADHU-ZIVBLGBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl-(methyl-5-acetamido-3,4,5-tridesoxy-4-iod-8,9-O-isopropyliden-α-D-manno-2-nonulopyranosid)onat 在 钯 sodium hydroxide 、 Dowex WX 4 (H+) 、 氢气 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 72.5h， 生成 5-acetamido-3,4,5-trideoxy-D-manno-2-nonulosonic acid
  参考文献：
  名称：

  Synthesis and Biological Properties ofN-Acetyl-4-deoxy-D-neuraminic Acid

  摘要：

  AbstractN‐Acetylneuraminic acid (1) can be transformed into the methyl α‐D‐ketoside 2 which, by reaction with methanesulfonyl chloride, yields the corresponding 4‐O‐mesylate 3 and the 4,7‐di‐O‐mesylate 4 as a by‐product. Compound 3 reacts with Nal giving the 4‐deoxy‐4‐iodo compound 5 with equatorial orientation of the I‐atom. As second product, the dihydrooxazole 6 is produced. Catalytic hydrogenation of 5 is followed by ester cleavage and removal of the isopropylidene group yielding the methyl α‐D‐ketoside 8 which affords the title compound, N‐acetyl‐4‐deoxyneuraminic acid (9), by reaction with fowl plague virus sialidase. Further biochemical activities of 8 and 9 are reported.

  DOI：

  10.1002/hlca.19860690837
• 作为产物：
  描述：

  methyl (methyl 5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-α-D-galacto-2-nonulopyrasidonate) 在 sodium iodide 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 3.67h， 生成 Methyl-(methyl-5-acetamido-3,4,5-tridesoxy-4-iod-8,9-O-isopropyliden-α-D-manno-2-nonulopyranosid)onat
  参考文献：
  名称：

  Synthesis and Biological Properties ofN-Acetyl-4-deoxy-D-neuraminic Acid

  摘要：

  AbstractN‐Acetylneuraminic acid (1) can be transformed into the methyl α‐D‐ketoside 2 which, by reaction with methanesulfonyl chloride, yields the corresponding 4‐O‐mesylate 3 and the 4,7‐di‐O‐mesylate 4 as a by‐product. Compound 3 reacts with Nal giving the 4‐deoxy‐4‐iodo compound 5 with equatorial orientation of the I‐atom. As second product, the dihydrooxazole 6 is produced. Catalytic hydrogenation of 5 is followed by ester cleavage and removal of the isopropylidene group yielding the methyl α‐D‐ketoside 8 which affords the title compound, N‐acetyl‐4‐deoxyneuraminic acid (9), by reaction with fowl plague virus sialidase. Further biochemical activities of 8 and 9 are reported.

  DOI：

  10.1002/hlca.19860690837