methyl 5-acetamido-9-amino-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid | 74545-37-2

• 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-amino-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid
• 英文别名: 9-Deoxy-9-amino-2-o-methyl-5-n-acetyl-alpha-d-neuraminic acid；(2R,4S,5R,6R)-5-acetamido-6-[(1R,2R)-3-amino-1,2-dihydroxypropyl]-4-hydroxy-2-methoxyoxane-2-carboxylic acid
• CAS: 74545-37-2
• 化学式: C₁₂H₂₂N₂O₈
• 分子量: 322.315
• InChiKey: LMLQOZLLZRAPEM-MIDKXNQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  172
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-9-amino-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid 在 sialate O-acetylesterase 碳酸氢铵 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 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-9-azido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)]nonate 在 1,3-丙二醇 sodium hydroxide 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 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

文献信息

• Synthesis of 5-N- and 9-N-thioacylated sialic acids
  作者：Rainer Isecke、Reinhard Brossmer

  DOI：10.1016/s0040-4020(01)90473-9

  日期：——

  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.