Hexaacetats der N-Acetylneuraminsaeure | 108740-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Hexaacetats der N-Acetylneuraminsaeure
• 英文别名: Methyl-2,4,7,8,9-penta-O-acetyl-5-acetylamino-3,5-dideoxy-L-glycero-β-L-altro-2-nonulopyranosidonat；methyl N-acetyl-2,4,7,8,9-penta-O-acetyl-β-D-neuraminate；methyl 2,4,7,8,9-penta-O-acetyl-N-acetyl-β-D-neuraminate；methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate；methyl 2,4,7,8,9-penta-O-acetyl-5-(acetylamino)-3,5-dideoxy-β-L-glycero-L-altro-2-nonulopyranosidonate；methyl (2R,4S,5R,6R)-5-acetamido-2,4-diacetyloxy-6-[(1R,2S)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 108740-39-2
• 化学式: C₂₂H₃₁NO₁₄
• 分子量: 533.486
• InChiKey: MFDZYSKLMAXHOV-AQXOQHEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.93
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  196.13
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Hexaacetats der N-Acetylneuraminsaeure 在 盐酸 、 乙酰氯 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 methyl 2-chloro-4,7,8,9-tetra-O-acetyl-N-acetyl-β-D-neuraminate
  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
• 作为产物：
  描述：

  N-acetylneuraminic acid methyl ester 生成 Hexaacetats der N-Acetylneuraminsaeure
  参考文献：
  名称：

  ZBIRAL, ERICH;SCHREINER, ERWIN;SALUNKHE, MAMIKRAO M.;SCHULZ, GERHARD;KLEI+, LIEBIGS ANN. CHEM.,(1989) N, C. 519-526

  摘要：

  DOI：

文献信息

• Studies on sialic acids. IV Synthesis of N-acetyl-D-neuraminic acid N-nucleoside analogs.
  作者：HARUO OGURA、HIDESHI FUJITA、KIMIO FURUHATA、MASAYOSHI ITOH、YOSHIYASU SHITORI

  DOI：10.1248/cpb.34.1479

  日期：——

  Some N-acetyl-D-neuraminec acid nucleoside analogs were synthesized. Methyl penta-O-acetyl-N-acetyl-D-neuraminate (1) was treated with trimethylsilyl-pyrimidine or -5-fluoropyrimidine and tin(IV) chloride to give a mixture of α- and β-anomers of N-nucleoside analogs. On the other hand, methyl tetra-O-acetyl-N-acetyl-2-chloro-β-D-neuraminate was allowed to react with trimethylsilyl-pyrimidine or -5-fluoropyrimidine under the Koenigs-Knorr reaction conditions to provide the β-anomer in a fair yield. The stereochemistry of these compounds was confirmed by measurements of the rate of hydrolysis of the glycosidic bond with water.

  合成了一些 N-乙酰基-D-神经氨酸核苷类似物。五-O-乙酰基-N-乙酰基-D-神经氨酸甲酯（1）经三甲基硅基嘧啶或-5-氟嘧啶和氯化锡（IV）处理后，得到 N-核苷类似物的α-和β-异构体混合物。另一方面，在柯尼希斯-克诺尔反应条件下，四-O-乙酰基-N-乙酰基-2-氯-β-D-神经氨酸甲酯可与三甲基硅基嘧啶或-5-氟嘧啶反应，以相当高的产率提供β-异构体。通过测量糖苷键与水的水解速度，证实了这些化合物的立体化学性质。
• Synthese von O-(5-Acetamido-3,5-didesoxy-d-glycero-α-d-galacto-2-nonulopyranosylonsäure) - (2→3) - O - β-d - galactopyranosyl - (1→3) - 2- acetamido -2 - desoxy-d-galactopyranose
  作者：Hans Paulsen、Ulrich von Deesen

  DOI：10.1016/0008-6215(88)84150-8

  日期：1988.5

  Synthese du disaccharide par l'addition du per-O-acetyl galactopyranose a l'azido-2 O-benzyl-1 desoxy-2 galactopyranoside. on y ajoute alors l'ester de l'acetamido-5 bromo-2 tetra-O-acetyl-4,7,8,9 tridesoxy-2,3,5 nonopyranosylulose-2 onique acide pour obtenir le trisaccharide correspondant

  在每个-O-乙酰基半乳糖吡喃糖上合成二糖，然后合成一个叠氮基-2 O-苄基-1脱氧基-2吡喃半乳糖苷。于a。aloute alors l'ester de l'acetamido-5 bromo-2 tetra-O-acetyl-4,7,8,9 tridesoxy-2,3,5 nonopyranosylulose-2 onique acide pour obtenir le trisaccharide
• Synthesis of 2-(5-cholesten-3.BETA.-yloxy) glycosides of N-acetyl-D-neuraminic acid derivatives.
  作者：SHINGO SATO、SYUJI FUJITA、KIMIO FURUHATA、HARUO OGURA、SHOJI YOSHIMURA、MASAYOSHI ITOH、YOSHIYASU SHITORI

  DOI：10.1248/cpb.35.4043

  日期：——

  2-(5-Cholesten-3β-yloxy)α- and β-glycosides of N-acetyl-D-neuraminic acid were prepared under various conditions through a Koenigs-Knorr-like reaction. The stereochemistry of the products was confirmed by analysis of the nuclear magnetic resonance and circular dichroism spectra.

  通过柯尼希斯-克诺尔类反应，在不同条件下制备了 N-乙酰基-D-神经氨酸的 2-(5-胆甾烯-3β-氧基)α-和β-糖苷。通过分析核磁共振和圆二色光谱证实了产物的立体化学性质。
• Ponpipom, M. M.; Bugianesi, R. L.; Shen, T.Y., Canadian Journal of Chemistry, 1980, vol. 58, p. 214 - 220
  作者：Ponpipom, M. M.、Bugianesi, R. L.、Shen, T.Y.

  DOI：——

  日期：——
• Zbiral, Erich; Schreiner, Erwin; Salunkhe, Mamikrao M., Liebigs Annalen der Chemie, 1989, p. 519 - 526
  作者：Zbiral, Erich、Schreiner, Erwin、Salunkhe, Mamikrao M.、Schulz, Gerhard、Kleineidam, Reinhard G.、Schauer, Roland

  DOI：——

  日期：——