5-acetamido-3,5-dideoxy-4-C-methyl-D-glycero-D-talo-nonulosonic acid | 134258-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetamido-3,5-dideoxy-4-C-methyl-D-glycero-D-talo-nonulosonic acid
• 英文别名: (2S,4R,5S,6R)-5-acetamido-2,4-dihydroxy-4-methyl-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 134258-63-2
• 化学式: C₁₂H₂₁NO₉
• 分子量: 323.3
• InChiKey: CHGIELQVYWSUKF-TXHIIHANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl-5-acetamido-7-O-acetyl-8,9-O-(1'-methyl-ethylidene)-3,5-dideoxy-β-D-manno-2,4-nonodiulopyranosidonic acid methyl ester 在 盐酸 、 sodium hydroxide 、 Amberlyst 15H⁺ 、 氯化锆(IV) 作用下， 反应 5.0h， 生成 5-acetamido-3,5-dideoxy-4-C-methyl-D-glycero-D-talo-nonulosonic acid
  参考文献：
  名称：

  Structural variations of N-acetylneuraminic acid, part 19: Synthesis of both epimeric pairs of the 4-C-methyl- and 4-deoxy-4-C-methyl- as well as of the ?-methylketoside of 4-deoxy-4-C-methylene-N-acetylneuraminic acid

  摘要：

  While the reaction of the 4-oxo-Neu 5 Ac derivative 2a with tributoxy methyl zirconate led exclusively to equatorial 4-C-methyl derivative 3a, the analogous reaction with tetramethyl zirconate yielded a 3:2 mixture of both diastereoisomers 3a and 4a. After removal of protecting groups the 5-acetamido-3,4-dideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulosoic acid 5a and 5-acetamido-3,4-dideoxy-4-C-methyl-D-glycero-D-talo-2-nonulosonic acid 6 a were obtained. The 4-C-methylene derivative was prepared by treatment of the same 4-oxo-derivative with CH2I2/Zn/Cp2ZrCl2. Subsequent hydrogenation led to both epimeric 4-deoxy-4-C-methyl derivatives 8a and 9a. Final removal of protecting groups gave the 5-acetamido-3,4,5-trideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulosonic acid 10a respectively the 5-acetamido-2,7-anhydro-4-C-methyl-3,4,5-trideoxy-D-glycero-D-talo-2-nonulosonic acid 11a. The beta-methylketosides of the 4-deoxy-4-C-methyl- (16) and 4-C-methylene-Neu 5 Ac (15) were prepared via the peracetylated derivatives to obtain modell substrates for enzymatic studies. Thus all free acids were tested for inhibition of CMP-sialate synthase. Only the 4-C-methylene compound 15 showed most unexpectedly a strong competitive inhibition of this enzyme.

  DOI：

  10.1007/bf00815172

文献信息

• Structural variations of N-acetylneuraminic acid, part 19: Synthesis of both epimeric pairs of the 4-C-methyl- and 4-deoxy-4-C-methyl- as well as of the ?-methylketoside of 4-deoxy-4-C-methylene-N-acetylneuraminic acid
  作者：Michael Hartmann、Rudolf Christian、Erich Zbiral

  DOI：10.1007/bf00815172

  日期：——

  While the reaction of the 4-oxo-Neu 5 Ac derivative 2a with tributoxy methyl zirconate led exclusively to equatorial 4-C-methyl derivative 3a, the analogous reaction with tetramethyl zirconate yielded a 3:2 mixture of both diastereoisomers 3a and 4a. After removal of protecting groups the 5-acetamido-3,4-dideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulosoic acid 5a and 5-acetamido-3,4-dideoxy-4-C-methyl-D-glycero-D-talo-2-nonulosonic acid 6 a were obtained. The 4-C-methylene derivative was prepared by treatment of the same 4-oxo-derivative with CH2I2/Zn/Cp2ZrCl2. Subsequent hydrogenation led to both epimeric 4-deoxy-4-C-methyl derivatives 8a and 9a. Final removal of protecting groups gave the 5-acetamido-3,4,5-trideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulosonic acid 10a respectively the 5-acetamido-2,7-anhydro-4-C-methyl-3,4,5-trideoxy-D-glycero-D-talo-2-nonulosonic acid 11a. The beta-methylketosides of the 4-deoxy-4-C-methyl- (16) and 4-C-methylene-Neu 5 Ac (15) were prepared via the peracetylated derivatives to obtain modell substrates for enzymatic studies. Thus all free acids were tested for inhibition of CMP-sialate synthase. Only the 4-C-methylene compound 15 showed most unexpectedly a strong competitive inhibition of this enzyme.