methyl-5-acetamido-7-O-acetyl-8,9-O-(1'-methyl-ethylidene)-3,5-dideoxy-β-D-manno-2,4-nonodiulopyranosidonic acid methyl ester | 128459-31-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-5-acetamido-7-O-acetyl-8,9-O-(1'-methyl-ethylidene)-3,5-dideoxy-β-D-manno-2,4-nonodiulopyranosidonic acid methyl ester
• 英文别名: methyl (2S,5S,6R)-5-acetamido-6-[(S)-acetyloxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-methoxy-4-oxooxane-2-carboxylate
• CAS: 128459-31-4
• 化学式: C₁₈H₂₇NO₁₀
• 分子量: 417.413
• InChiKey: URATWOZAGQEZBM-DWJZYCCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.55
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  135.69
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  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-galacto-2-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
• 作为产物：
  描述：

  Methyl-5-(acetylamino)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester 在 四氧化钌 、 potassium metaperiodate 、 potassium carbonate 作用下， 以 吡啶 、 氯仿 为溶剂， 反应 0.5h， 生成 methyl-5-acetamido-7-O-acetyl-8,9-O-(1'-methyl-ethylidene)-3,5-dideoxy-β-D-manno-2,4-nonodiulopyranosidonic acid methyl ester
  参考文献：
  名称：

  Structural variations of N-Acetylneuraminic acid, 12: A new useful approach to 4-epi- and 8-epi-N-Acetylneuraminic acid

  摘要：

  DOI：

  10.1007/bf00811129

文献信息

• HARTMANN, MICHAEL;ZBIRAL, ERICH, MONATSH. CHEM., 120,(1989) N0, C. 899-906
  作者：HARTMANN, MICHAEL、ZBIRAL, ERICH

  DOI：——

  日期：——