methyl (methyl 5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-4-O-methanesulfonyl-α-D-glycero-D-galacto-2-nonulopyranosid)onate | 110390-68-6

• 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-3,5-dideoxy-8,9-O-isopropylidene-4-O-methanesulfonyl-α-D-glycero-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl (2R,4S,5S,6R)-5-acetamido-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2-methoxy-4-methylsulfonyloxyoxane-2-carboxylate
• CAS: 110390-68-6
• 化学式: C₁₇H₂₉NO₁₁S
• 分子量: 455.483
• InChiKey: UVPUEQJSCCEQMI-ZAGDVDGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  164
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (methyl 5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-4-O-methanesulfonyl-α-D-glycero-D-galacto-2-nonulopyranosid)onate 在 钯 sodium hydroxide 、 Dowex WX 4 (H+) 、 氢气 、 sodium iodide 作用下， 以 吡啶 、 甲醇 、 丙酮 为溶剂， 反应 55.5h， 生成 methyl 5-acetamido-3,4,5-trideoxy-α-D-manno-non-2-ulopyranosidonic 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-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 对甲苯磺酸 作用下， 以 吡啶 为溶剂， 反应 4.67h， 生成 methyl (methyl 5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-4-O-methanesulfonyl-α-D-glycero-D-galacto-2-nonulopyranosid)onate
  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

文献信息

• Synthesis and Biological Properties ofN-Acetyl-4-deoxy-D-neuraminic Acid
  作者：Heinz-Werner Hagedorn、Reinhard Brossmer

  DOI：10.1002/hlca.19860690837

  日期：1986.12.10

  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.