methyl 5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid | 143791-27-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid
• CAS: 143791-27-9
• 化学式: C₁₂H₂₀N₄O₈
• 分子量: 348.313
• InChiKey: JZLCECOPUOLETR-MIDKXNQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  194.31
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid 在 1,3-丙二醇 氢气 作用下， 以 水 为溶剂， 反应 2.0h， 以0.41 g的产率得到methyl 5-acetamido-9-amino-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid
  参考文献：
  名称：

  Synthesis of 5-N- and 9-N-thioacylated sialic acids

  摘要：

  N-Thioacylation of neuraminic acid methyl alpha-glycoside (5) with O-ethyl thioformate (1), methyl dithioacetate (2), and methyl dithiopropionate (3) afforded N-thioformyl, N-thioacetyl, and N-thiopropionyl neuraminic acid derivatives 6a-c in high yield. Cleavage of the glycosides was accomplished either by acid hydrolysis or by sialidase treatment. Alternatively, 5-N-thioacylneuraminic acids were produced from the corresponding N-thioacyl-D-mannosamines 7a-c and pyruvate employing N-acetylneuraminate pyruvate lyase. The sialidase-resistant methyl alpha-thioglycoside of N-thioacetylneuraminic acid (10) was also prepared. N-Acetyl-9-deoxy-9-thioacetamido neuraminic acid (19) was obtained either directly by reaction of N-acetyl-9-amino-9-deoxyneuraminic acid (17) with methyl dithioacetate (2) or via its methyl alpha-glycoside 18. Compound 17 was produced from the methyl a-glycoside of 9-O-tosylated methyl ester 12 via the azide 13. -For the 5-N-thioacyl sialic acids 6a-c and 8a-c as well as for the 9-deoxy-9-thioacetamido derivatives 18 and 19 some biological properties are reported.

  DOI：

  10.1016/s0040-4020(01)90473-9
• 作为产物：
  描述：

  methyl (methyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 吡啶 、 sodium hydroxide 、 sodium azide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 41.0h， 生成 methyl 5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid
  参考文献：
  名称：

  Synthesis of 5-N- and 9-N-thioacylated sialic acids

  摘要：

  N-Thioacylation of neuraminic acid methyl alpha-glycoside (5) with O-ethyl thioformate (1), methyl dithioacetate (2), and methyl dithiopropionate (3) afforded N-thioformyl, N-thioacetyl, and N-thiopropionyl neuraminic acid derivatives 6a-c in high yield. Cleavage of the glycosides was accomplished either by acid hydrolysis or by sialidase treatment. Alternatively, 5-N-thioacylneuraminic acids were produced from the corresponding N-thioacyl-D-mannosamines 7a-c and pyruvate employing N-acetylneuraminate pyruvate lyase. The sialidase-resistant methyl alpha-thioglycoside of N-thioacetylneuraminic acid (10) was also prepared. N-Acetyl-9-deoxy-9-thioacetamido neuraminic acid (19) was obtained either directly by reaction of N-acetyl-9-amino-9-deoxyneuraminic acid (17) with methyl dithioacetate (2) or via its methyl alpha-glycoside 18. Compound 17 was produced from the methyl a-glycoside of 9-O-tosylated methyl ester 12 via the azide 13. -For the 5-N-thioacyl sialic acids 6a-c and 8a-c as well as for the 9-deoxy-9-thioacetamido derivatives 18 and 19 some biological properties are reported.

  DOI：

  10.1016/s0040-4020(01)90473-9