Methyl-4,7,8,9-tetra-O-acetyl-5-acetylamino-3,5-didesoxy-β-L-glycero-D-galacto-2-nonulopyranosidonsaeuremethylester | 99395-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-4,7,8,9-tetra-O-acetyl-5-acetylamino-3,5-didesoxy-β-L-glycero-D-galacto-2-nonulopyranosidonsaeuremethylester
• 英文别名: methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-L-glycero-D-galacto-2-nonulopyranosidonic acid methyl ester；methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-L-glycero-β-L-altro-2-nonulopyranosidonic acid methyl ester；Methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-L-glycero-D-galacto-β-2-nonulopyranosidonsaeuremethylester；methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-methoxy-6-[(1S,2S)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 99395-95-6
• 化学式: C₂₁H₃₁NO₁₃
• 分子量: 505.476
• InChiKey: BDVAGIAWBFWKLD-JQCUPLDDSA-N

物化性质

• 沸点：
  593.7±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.85
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  179.06
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Methyl-4,7,8,9-tetra-O-acetyl-5-acetylamino-3,5-didesoxy-β-L-glycero-D-galacto-2-nonulopyranosidonsaeuremethylester 在 咪唑 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 Methyl-5-acetylamino-4,9-bis-O-(t-butyldimethylsilyl)-3,5-didesoxy-β-L-glycero-D-galacto-2-nonulopyranosidonsaeuremethylester
  参考文献：
  名称：

  Strukturelle Abwandlungen anN-Acetylneuramins�ure, 3

  摘要：

  DOI：

  10.1007/bf00798282
• 作为产物：
  描述：

  methyl-5-acetamido-4,7,9-tri-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonic acid methyl ester 在 4-二甲氨基吡啶 、 ruthenium(IV) oxide 、 硼烷铵络合物 、 potassium metaperiodate 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 Methyl-4,7,8,9-tetra-O-acetyl-5-acetylamino-3,5-didesoxy-β-L-glycero-D-galacto-2-nonulopyranosidonsaeuremethylester
  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

• Salunkhe, Mamikroo; Hartmann, Michael; Schmid, Walter, Liebigs Annalen der Chemie, 1988, p. 187 - 190
  作者：Salunkhe, Mamikroo、Hartmann, Michael、Schmid, Walter、Zbiral, Erich

  DOI：——

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

  DOI：——

  日期：——
• SALUNKHE, MAMIKROO;HARTMANN, MICHAEL;SCHMID, WALTHER;ZBIRAL, ERICH, LIEBIGS ANN. CHEM.,(1988) N 2, 187-189
  作者：SALUNKHE, MAMIKROO、HARTMANN, MICHAEL、SCHMID, WALTHER、ZBIRAL, ERICH

  DOI：——

  日期：——
• Strukturelle Abwandlungen an N-Acetylneuramins�ure, 25. Mitt.: Synthese von Methyl-2-?-glycosiden von 4-epi-, 7-epi-, 8-epi- und 7,8-bis-epi-N-Acetylneuramins�ure
  作者：B. P. Bandgar、E. Zbiral

  DOI：10.1007/bf00811116

  日期：1991.12

  The alpha-methylketoside of N-acetylneuraminic acid methylester (4) is transformed via the deacetylated compound 5 into the 9,8-O-isopropylidenderivative 6 which could be oxidized regioselectivity by RuO4 to the corresponding 4-oxo-sialic acid analogue 7. Reduction with the borane-ammonia complex produces a 1:1 mixture of 6 and the desired alpha-methylketoside of 9,8-O-isopropyliden-4-epi-N-acetyl-neuraminic acid methylester (8). Removing of the isopropylidene group gives the alpha-methylketoside of 4-epi-N-acetylneuraminic acid alpha-methylketoside (10). On the other hand compound 5 was turned into the 4,8,9-tri-O-t-butyldimethylsilylderivative 11 a from which the corresponding 7-oxo-compound 12 by oxidation with RuO4 derives. The reduction of 12 with BH3 - NH3 yielded a 1:1 mixture of the starting material 11 a and the desired 7-epi-derivative 13 a which gives either via the purified peracetylated alpha-methylketosid of 7-epi-N-acetylneuraminic acid methylester (14) or a direct saponification the sodium salt of 7-epi-N-acetylneuraminic acid-alpha-methylketoside (15).Applying the Konigs-Knorr procedure to the peracetylated 8-epi-N-acetylneuraminic acid methylester (16) gives rise to the formation of a 1:1 mixture of the corresponding alpha- and beta-methylketosides 17 and 18 besides traces of the corresponding 2,3-dideoxy-2,3-dideohydro-sialic acid derivative 19. After chromatographic separation of 17 further saponification leads to the sodium salt of 8-epi-N-acetylneuraminic acid-alpha-methylketoside (20). In an analogous procedure the sodium salt of 7,8-di-epi-N-acetylneuraminic acid-alpha-methylketoside (25) was prepared starting from the peracetylated 7,8-di-epi-N-acetylneuraminic acid methylester (21), whereby a mixture of the alpha- and beta-methylketosides 22 and 23 was formed in a ratio 95:5 besides traces of the peracetylated 2,3-dideoxy-2,3-didehydrosialic acid methylester (24).