allyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid | 55560-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid
• 英文别名: NeuAc(a)-O-allyl；(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-prop-2-enoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 55560-08-2
• 化学式: C₁₄H₂₃NO₉
• 分子量: 349.338
• InChiKey: BWOMKFNRLLGJEU-KXEMTNKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid 在 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 sodium;(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-[3-[2-(prop-2-enoylamino)ethylsulfanyl]propoxy]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  结合小麦胚芽凝集素和抗体的N-乙酰神经氨酸抗原共聚物的合成。

  摘要：

  DOI：

  10.1016/0008-6215(88)85068-7
• 作为产物：
  描述：

  Methyl (allyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 sodium hydroxide 作用下， 以93%的产率得到allyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid
  参考文献：
  名称：

  Synthesis of protein conjugates and analogues of N-acetylneuraminic acid

  摘要：

  N-乙酰神经酰胺酸（1）是通过改进的程序从中国燕子的唾液腺黏蛋白中制备的，该程序使用酸性树脂水解。化合物1通过新的两步程序转化为已知的乙酰氯乙酰神经酸（3）。对3进行Koenigs-Knorr糖基化，然后通过随后的还原臭氧裂解2-丙烯基α-糖苷制得关键的醛前体7和8，它们通过还原胺化与牛血清白蛋白或破伤风类毒素结合。研究了影响合并程度的因素。还合成了一系列在战略性功能上修改的N-乙酰神经酰胺酸类似物。关键词：唾液酸，N-乙酰神经酰胺酸，新糖蛋白，牛血清白蛋白，破伤风类毒素。

  DOI：

  10.1139/v90-313

文献信息

• Synthesis of Methyl and Allyl alpha-Glycosides of N-Acetylneuraminic Acid in the Absence of Added Promoter.
  作者：Leonid O. Kononov、Göran Magnusson、Marina I. Ferrero、Cesare Rol、Giovanni V. Sebastiani、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0141

  日期：——

  Sialic acids, especially N-acetylneuraminic acid, are present (as alpha-glycosides) on biologically important glycolipids and glycoproteins. Synthesis of sialic acid-containing oligosaccharides is therefore a prerequisite for many glycobiological studies. Such syntheses often use simple sialyl glycosides as starting materials. Their preparation usually employs heavy metal salts or other toxic and/or expensive promoters.' As a consequence, only few of these methods are suitable for large-scale preparations.We wish to report a simple, alpha/beta-selective, and high-yielding preparative procedure for the methyl sialosides 5 and 6, and the allyl sialoside 7 (Scheme 1), that avoids the use of specially added promoter (although HCl liberated during the reaction probably promotes the reaction). A few examples of 'non-catalyzed' glycosylations with acetobromohexosides, leading to de-O-acetylated methyl glycosides, have been reported.(2) Furthermore, various bromo analogs of 4 were recently used for sialylation of methanol and benzyl alcohol in the absence of metal salt promoters (but in the presence of collidinium salt) to give glycosides in 70-95% yield, with an alp ratio of 1:1-9:1.(3)The known O-acetylated N-acetylneuraminic acid(4) (1) and methyl ester(5,6) (2) were treated separately with HCl/CH2Cl2 to give acetochloroneuraminic acid(4) (3) and methyl ester(5) (4) of 90-95% purity according to H-1 NMR. Compounds 3 and 4 were each dissolved in methanol and the mixtures were kept at room temperature. According to TLC analysis, compound 3 was consumed within 1 min, whereas compound 4 required a reaction time of 1 h. Three different batches of methanol were investigated, with virtually identical results.
• ROY, RENE;LAFERRIERE, CRAIG A., CARBOHYDR. RES., 177,(1988) C1-64
  作者：ROY, RENE、LAFERRIERE, CRAIG A.

  DOI：——

  日期：——
• Synthesis of protein conjugates and analogues of <i>N</i>-acetylneuraminic acid
  作者：René Roy、Craig A. Laferrière

  DOI：10.1139/v90-313

  日期：1990.11.1

  N-Acetylneuraminic acid (1) was prepared from the salivary gland mucins of the Chinese swiftlet by an improved procedure using acidic resin hydrolysis. Compound 1 was transformed into the known acetochloroneuraminic acid (3) by a new two-step procedure. Koenigs–Knorr glycosylation of 3 followed by subsequent reductive ozonolysis of the 2-propenyl α-glycoside afforded the key aldehyde precursors 7 and 8, which were coupled to bovine serum albumin or tetanus toxoid by reductive amination. The factors influencing the extent of incorporation were investigated. A series of N-acetylneuraminic acid analogues modified at strategic functionalities were also synthesized. Keywords: sialic acid, N-acetylneuraminic acid, neoglycoproteins, bovine serum albumin, tetanus toxoid.

  N-乙酰神经酰胺酸（1）是通过改进的程序从中国燕子的唾液腺黏蛋白中制备的，该程序使用酸性树脂水解。化合物1通过新的两步程序转化为已知的乙酰氯乙酰神经酸（3）。对3进行Koenigs-Knorr糖基化，然后通过随后的还原臭氧裂解2-丙烯基α-糖苷制得关键的醛前体7和8，它们通过还原胺化与牛血清白蛋白或破伤风类毒素结合。研究了影响合并程度的因素。还合成了一系列在战略性功能上修改的N-乙酰神经酰胺酸类似物。关键词：唾液酸，N-乙酰神经酰胺酸，新糖蛋白，牛血清白蛋白，破伤风类毒素。
• Synthesis of antigenic copolymers of N-acetylneuraminic acid binding to wheat germ agglutinin and antibodies
  作者：René Roy、Craig A. Laferrière

  DOI：10.1016/0008-6215(88)85068-7

  日期：1988.6