methyl [O-methyl-(5-acetamido-9-azido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)]nonate | 160555-87-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [O-methyl-(5-acetamido-9-azido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)]nonate
• 英文别名: methyl (methyl 5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• CAS: 160555-87-3
• 化学式: C₁₃H₂₂N₄O₈
• 分子量: 362.34
• InChiKey: XCQDHQAEFYFAFV-CTAKWSDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.81
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  183.31
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl [O-methyl-(5-acetamido-9-azido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)]nonate 在 sialate O-acetylesterase 、 1,3-丙二醇 sodium hydroxide 、 氢气 、 碳酸氢铵 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 21.0h， 生成 ammonium 5-acetamido-3,5,9-trideoxy-9-thioacetamido-D-glycero-D-galacto-2-nonulopyranosonate
  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 [O-methyl-(5-acetamido-3,5-dideoxy-9-O-(4-toluenesulfonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl)]nonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以66%的产率得到methyl [O-methyl-(5-acetamido-9-azido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)]nonate
  参考文献：
  名称：

  Photodegradation and inhibition of drug-resistant influenza virus neuraminidase using anthraquinone–sialic acid hybrids

  摘要：

  设计的蒽醌-唾液酸杂化物不仅能有效降解非耐药神经氨酸酶，还能有效降解耐药神经氨酸酶，这是抗流感治疗的重要靶点。在没有任何添加剂和中性条件下使用长波长紫外线辐射实现降解。此外，杂种在光照射下有效抑制神经氨酸酶活性。

  DOI：

  10.1039/c2cc38742e

文献信息

• SIALIC ACID DERIVATIVES
  申请人：BROSSMER Reinhard

  公开号：US20160362436A1

  公开（公告）日：2016-12-15

  Sialic acid derivatives of the formula (I)

  公式（I）的唾液酸衍生物