methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate | 866332-57-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate
• CAS: 866332-57-2
• 化学式: C₂₇H₃₂F₃NO₁₂S
• 分子量: 651.612
• InChiKey: QKGQPYPFWAMVFT-RNCZJOPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  169.83
• 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-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate 在 四氮唑 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 水 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 0.75h， 生成 methyl 4,7,8-tri-O-acetyl-3,5-dideoxy-9-O-(methyl-5-trifluoroacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-5-trifluoroacetamido-D-glycero-D-galacto-non-2-ulopyranosidonate
  参考文献：
  名称：

  N-Trifluoroacetyl Sialyl Phosphite Donors for the Synthesis of α(2 → 9) Oligosialic Acids

  摘要：

  A new method for the synthesis of alpha(2 -> 9) oligosialic acids is developed using phosphite sialyl donors that are protected with a C-5 N-trifluoroacetyl (NHTFA) substituent. Compared with conventional donors, these donors gave a higher degree of alpha-anomeric selectivity during glycosidic bond formation and better yields during iterative sialylation in the synthesis of oligosialic acids.

  DOI：

  10.1021/ol0515210
• 作为产物：
  描述：

  (2S,4S,5R,6R)-5-Amino-4-hydroxy-2-p-tolylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 17.5h， 生成 methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosidonate
  参考文献：
  名称：

  N-Trifluoroacetyl Sialyl Phosphite Donors for the Synthesis of α(2 → 9) Oligosialic Acids

  摘要：

  A new method for the synthesis of alpha(2 -> 9) oligosialic acids is developed using phosphite sialyl donors that are protected with a C-5 N-trifluoroacetyl (NHTFA) substituent. Compared with conventional donors, these donors gave a higher degree of alpha-anomeric selectivity during glycosidic bond formation and better yields during iterative sialylation in the synthesis of oligosialic acids.

  DOI：

  10.1021/ol0515210

文献信息

• 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 Sialyl Lewis^a Antigen and the Effective Anticancer Activity of Its Bacteriophage Qβ Conjugate as an Anticancer Vaccine
  作者：Zahra Rashidijahanabad、Sherif Ramadan、Nicholas A. O'Brien、Athar Nakisa、Shuyao Lang、Howard Crawford、Jeffrey C. Gildersleeve、Xuefei Huang

  DOI：10.1002/anie.202309744

  日期：2023.11.20

  develop an effective sialyl Lewisa based vaccine, the stereoselective synthesis of sialyl Lewisa tetrasaccharide was accomplished. The glycan was covalently conjugated with a powerful carrier, bacteriophage Qβ, which induced higher levels of and persistent anti-sialyl Lewisa IgG antibody responses, thus providing significant tumor protection in a metastatic cancer model in mice.

  Sialyl Lewisa 是一种有吸引力的碳水化合物相关癌症抗原。为了开发一种有效的唾液酸 Lewis疫苗，完成了唾液酸 Lewis一种四糖的立体选择性合成。该聚糖与强大的载体噬菌体 Qβ 共价偶联，可诱导更高水平的和持续的抗唾液酸 Lewisa IgG 抗体反应，从而在小鼠转移性癌症模型中提供显著的肿瘤保护。