Natrium-(methyl-5-acetamido-3,5-dideoxy-D-glycero-α-L-altro-2-nonulopyranosid)onat | 140219-75-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Natrium-(methyl-5-acetamido-3,5-dideoxy-D-glycero-α-L-altro-2-nonulopyranosid)onat
• 英文别名: methyl 5-N-acetyl-α-D-neuraminate sodium salt；sodium;(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-methoxy-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 140219-75-6
• 化学式: C₁₂H₂₀NO₉*Na
• 分子量: 345.282
• InChiKey: WAEZEQUBHGTBMQ-LGXBVESSSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -7.55
• 重原子数：
  23
• 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：
  169
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Natrium-(methyl-5-acetamido-3,5-dideoxy-D-glycero-α-L-altro-2-nonulopyranosid)onat 、 碘甲烷 在 dimsylpotassium 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以68%的产率得到methyl onate
  参考文献：
  名称：

  还原裂解法分析含唾液酸的碳水化合物的结构

  摘要：

  使用完全甲基化的甲基α-和β-N-乙酰神经氨酸（分别为1和2）研究了还原裂解法在含唾液酸的碳水化合物的结构分析中的适用性。两种化合物在硼烷二甲硫醚和三氟化硼醚化物的存在下对还原裂解是完全稳定的，但是在三乙基硅烷和促进剂如三甲基甲硅烷基三氟甲磺酸盐，三氟化硼醚化物或三甲基甲硅烷基甲烷磺酸盐和三氟化硼醚化物的混合物的存在下缓慢降解。但是，在用硼氢化钠选择性还原1和2的酯基后，产物（分别为3和4）进行了快速还原裂解，得到了预期的脱水醛糖醇，通过GLC-分析将其表征为乙酸盐（8和11）。小姐。主要产物还通过1 H NMR光谱表征为其苯甲酸酯（9）。使用3'-唾液乳糖，即α-Neu5Ac-（2-> 3）-β-D-Galp-（1-4）-D-Glc证明了这种分析方法的有用性。甲基化和酯还原的三糖（13）用Me2S.BH3-BF3.ET2O还原裂解，产物被乙酰化。通过GLC-MS分析发现，预期末端（非还原

  DOI：

  10.1016/0008-6215(93)84124-o
• 作为产物：
  描述：

  (1S,2R)-1-((2R,3R,4S)-3-乙酰氨基-4-乙酰氧基-6-氯-6-(甲氧基羰基 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 ammonia borane 、 四氧化钌 、 3 A molecular sieve 、 水 、 sodium methylate 、 溶剂黄146 、 silver carbonate 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 86.5h， 生成 Natrium-(methyl-5-acetamido-3,5-dideoxy-D-glycero-α-L-altro-2-nonulopyranosid)onat
  参考文献：
  名称：

  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

  摘要：

  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).

  DOI：

  10.1007/bf00811116

文献信息

• Structural analysis of sialic acid-containing carbohydrates by the reductive-cleavage method
  作者：Vandana Srivastava、Gary R. Gray

  DOI：10.1016/0008-6215(93)84124-o

  日期：1993.10

  was investigated using fully methylated methyl alpha- and beta-N-acetylneuraminic acid (1 and 2, respectively). Both compounds were fully stable to reductive cleavage in the presence of borane dimethylsulfide and boron trifluoride etherate but were slowly degraded in the presence of triethylsilane and promoters such as trimethylsilyl trifluoromethanesulfonate, boron trifluoride etherate, or a mixture

  使用完全甲基化的甲基α-和β-N-乙酰神经氨酸（分别为1和2）研究了还原裂解法在含唾液酸的碳水化合物的结构分析中的适用性。两种化合物在硼烷二甲硫醚和三氟化硼醚化物的存在下对还原裂解是完全稳定的，但是在三乙基硅烷和促进剂如三甲基甲硅烷基三氟甲磺酸盐，三氟化硼醚化物或三甲基甲硅烷基甲烷磺酸盐和三氟化硼醚化物的混合物的存在下缓慢降解。但是，在用硼氢化钠选择性还原1和2的酯基后，产物（分别为3和4）进行了快速还原裂解，得到了预期的脱水醛糖醇，通过GLC-分析将其表征为乙酸盐（8和11）。小姐。主要产物还通过1 H NMR光谱表征为其苯甲酸酯（9）。使用3'-唾液乳糖，即α-Neu5Ac-（2-> 3）-β-D-Galp-（1-4）-D-Glc证明了这种分析方法的有用性。甲基化和酯还原的三糖（13）用Me2S.BH3-BF3.ET2O还原裂解，产物被乙酰化。通过GLC-MS分析发现，预期末端（非还原
• 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).