Allyl 5-amino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid | 131087-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Allyl 5-amino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid
• 英文别名: Neu(a)-O-allyl；(2R,4S,5R,6R)-5-amino-4-hydroxy-2-prop-2-enoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 131087-89-3
• 化学式: C₁₂H₂₁NO₈
• 分子量: 307.301
• InChiKey: QBFXCNCCYFAGMF-MIDKXNQYSA-N

物化性质

• 沸点：
  614.2±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  163
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Allyl 5-amino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid 在 吡啶 、 三甲基氯硅烷 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 methyl (2R,4S,5R,6R)-5-[[2-[(2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-methoxycarbonyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxan-2-yl]oxyacetyl]amino]-4-acetyloxy-2-prop-2-enoxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of Neu5Acα(2→5)Neu5Gc:  The Building Block of Oligo/Poly(→5-O_glycolylNeu5Gcα2→) Chains in Sea Urchin Egg Cell Surface Glycoprotein

  摘要：

  The synthesis of a sialic acid dimer derivative, Neu5Acalpha(2-->5)Neu5Gc, is described. The synthetic strategy is based on the use of allyl alcohol to achieve an exclusive alpha-sialylation product. The allyloxy group is also a latent glycolic acid that provides the subsequent coupling with neuraminate with minimal protection-deprotection manipulations.

  DOI：

  10.1021/jo025988p
• 作为产物：
  描述：

  allyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,54-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonic acid methyl ester 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 以95%的产率得到Allyl 5-amino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonic acid
  参考文献：
  名称：

  亚磷酸唾液酸供体在α（2→9）低唾液酸合成中的作用

  摘要：

  亚磷酸酯供体和异头硫醇甲酚保护的受体的组合，在唾液酸的C-5处均具有TFA保护基，在唾液酸化中提供了良好的α-选择性和产率。尽管使用亚磷酸酯二唾液酸供体和二唾液酸受体的会聚合成策略有效地组装了四唾液酸，但是仍然需要克服α-端基异构体的低α-选择性并对其进行纯化。此外，将单唾液酸和二唾液酸分别缀合在载体蛋白，匙孔血蓝蛋白上。建议使用酶水解方法估算蛋白质偶联物上唾液酸的量。

  DOI：

  10.1016/j.tet.2009.04.022

文献信息

• 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。
• Phosphite-based sialic acid donors in the synthesis of α(2→9) oligosialic acids
  作者：Chang-Ching Lin、Avijit Kumar Adak、Jia-Cherng Horng、Chun-Cheng Lin

  DOI：10.1016/j.tet.2009.04.022

  日期：2009.6

  The combination of a phosphite donor and an anomeric thiocresol-protected acceptor, both with a TFA protecting group at C-5 of the sialic acid, provides good α-selectivity and yield in sialylation. Although the convergent synthetic strategy of using a phosphite disialo-donor and a disialo-acceptor assembles tetra-sialic acid efficiently, overcoming the low α-selectivity of α-anomer and purifying it

  亚磷酸酯供体和异头硫醇甲酚保护的受体的组合，在唾液酸的C-5处均具有TFA保护基，在唾液酸化中提供了良好的α-选择性和产率。尽管使用亚磷酸酯二唾液酸供体和二唾液酸受体的会聚合成策略有效地组装了四唾液酸，但是仍然需要克服α-端基异构体的低α-选择性并对其进行纯化。此外，将单唾液酸和二唾液酸分别缀合在载体蛋白，匙孔血蓝蛋白上。建议使用酶水解方法估算蛋白质偶联物上唾液酸的量。
• Stereoselective Synthesis of Neu5Acα(2→5)Neu5Gc:  The Building Block of Oligo/Poly(→5-<i>O</i>_g_lycolylNeu5Gcα2→) Chains in Sea Urchin Egg Cell Surface Glycoprotein
  作者：Gang-Ting Fan、Chen-Chang Lee、Chun-Cheng Lin、Jim-Min Fang

  DOI：10.1021/jo025988p

  日期：2002.10.1

  The synthesis of a sialic acid dimer derivative, Neu5Acalpha(2-->5)Neu5Gc, is described. The synthetic strategy is based on the use of allyl alcohol to achieve an exclusive alpha-sialylation product. The allyloxy group is also a latent glycolic acid that provides the subsequent coupling with neuraminate with minimal protection-deprotection manipulations.