methyl [O-methyl-(5-acetamido-3,5-dideoxy-9-O-(4-toluenesulfonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl)]nonate | 160555-86-2

• 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-3,5-dideoxy-9-O-(4-toluenesulfonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl)]nonate
• 英文别名: methyl (methyl 5-acetamido-3,5-dideoxy-9-O-p-toluenesulfonyl-D-glycero-α-D-galacto-2-nonulopyranosid)onate；methyl (methyl 5-acetamido-3,5-dideoxy-9-O-p-tolylsulfonyl-D-glycero-α-galacto-2-nonulopyranosid)onate
• CAS: 160555-86-2
• 化学式: C₂₀H₂₉NO₁₁S
• 分子量: 491.516
• InChiKey: LCZMEOWUCCLQNV-UMCYSPNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.41
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  177.92
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl [O-methyl-(5-acetamido-3,5-dideoxy-9-O-(4-toluenesulfonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl)]nonate 在 1,3-丙二醇 sodium hydroxide 、 sodium azide 、 氢气 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 43.0h， 生成 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 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 5.0h， 以69%的产率得到methyl [O-methyl-(5-acetamido-3,5-dideoxy-9-O-(4-toluenesulfonyl)-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

• 10.1016/s0008-6215(99)00058-0
  作者：Liav, Avraham、Hansjergen, Joyce A.、Achyuthan, Komandoor E.、Shimasaki, Craig D.

  DOI：10.1016/s0008-6215(99)00058-0

  日期：——

  5-bromo-indol-3-ol to give the chromogenic product (13). Deprotection of 13 gave 5-bromo-indol-3-yl 4,7-di-O-methyl-Neu5Ac (5). The product 5 was specifically cleaved by sialidase from either influenza A or influenza B virus to give an indigo-blue precipitate, but was not cleaved by several bacterial or viral sialidases tested. The properties of product 5 relative to a fluorescent substrate for sialidase were also documented

  将N-乙酰神经氨酸（Neu5Ac）转化为甲酯甲基酮苷-8,9-环氧衍生物（8）。8的甲基化，然后脱保护，得到4,7-二-O-甲基-Neu5Ac（10）。将化合物10转化为相应的甲酯-氯乙酸甲酯衍生物，随后将其与5-溴-吲哚-3-醇偶联，得到生色产物（13）。13的脱保护得到5-溴-吲哚-3-基4，7-二-O-甲基-Neu5Ac（5）。产物5被唾液酸酶特异性地从甲型流感病毒或乙型流感病毒中裂解，得到靛蓝色沉淀，但没有被所测试的几种细菌或病毒唾液酸酶裂解。还记录了产物5相对于唾液酸酶的荧光底物的性质。